- Efficient ring opening reactions of N-tosyl aziridines with amines and water in presence of catalytic amount of cerium(IV) ammonium nitrate
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While methyl- and benzylamines opened N-tosyl aziridines 1 very efficiently in acetonitrile with complete regio- and stereoselectivity to give the corresponding diamines 2 and 3, respectively, in excellent yields, similar openings with water could only be achieved in the presence of a catalytic amount of cerium(IV) ammonium nitrate under very mild conditions furnishing the amino alcohols 4.
- Chakraborty, Tushar K.,Ghosh, Animesh,Raju, T. Venugopal
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Read Online
- Synthesis of 2-Aminophosphates via SN2-Type Ring Openings of Aziridines with Organophosphoric Acids
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The synthesis of 2-aminophosphates is achieved by a SN2-type ring opening reaction of various N-protected or free aziridines with phosphoric acids in a regiospecific and/or enantiospecific way. A one-pot, two-step procedure is also developed enabling direct access to 2-aminophosphates from olefins without isolation of the aziridine intermediates.
- Wang, Yang,Liu, Bing-Yi,Yang, Gaosheng,Chai, Zhuo
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Read Online
- Conversion of aziridines to oxazolidines through geminal difunctionalization of vinyl arenes or by tandem ring-opening/closing reaction of aziridine itself
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One pot synthesis of 1,3-oxazolidines derivatives was developed by two different approaches. Aziridines were used in the first approach instead of amino alcohol. Whereas, in the second approach we have developed an unprecedented reaction where aziridine i
- Ghosal, Nirnita Chakraborty,Santra, Sougata,Zyryanov, Grigory V.,Hajra, Alakananda,Majee, Adinath
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Read Online
- Ceric ammonium nitrate (CAN) catalyzed ring cleavage of N-tosyl aziridines: A potential tool for solution phase library generation
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A range of N-tosylaziridines is cleaved with NaN3, H2O, MeOH to synthesize vicinal azidoamines, aminols and amino ethers in good to excellent yields catalyzed by ceric ammonium nitrate and used in solution phase library synthesis.
- Chandrasekhar,Narsihmulu,Shameem Sultana
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Read Online
- Zirconyl nitrate mediated regioselective ring opening of epoxides and aziridines: an easy synthesis of β-nitrato-alcohols and -sulfonamides
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Epoxides and aziridines are cleaved efficiently and regioselectively in the presence of zirconyl nitrate at room temperature to afford the corresponding β-nitrato-alcohols and -sulfonamides, respectively, in high yields.
- Das, Biswanath,Krishnaiah, Maddeboina,Venkateswarlu, Katta
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Read Online
- A tandem process for the synthesis of β-aminoboronic acids from aziridines with haloamine intermediates
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An unprecedented synthetic strategy is devised to generate β-aminoboronic acids from aziridines via a sequential process involving 1,2-iodoamine formation and radical borylation under light irradiation. A variety of aziridines including multiply substituted aziridines have been successfully employed as synthetic precursors, expanding their synthetic utility compared to previous methods. Mechanistic studies suggest that the boron source plays a unique role in the borylation step, and in the formation of haloamine intermediates.
- Park, Subin,Koo, Jangwoo,Kim, Weonjeong,Lee, Hong Geun
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p. 3767 - 3770
(2022/04/07)
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- Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines
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Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea
- Biletskyi, Bohdan,Kong, Lingyu,Tenaglia, Alphonse,Clavier, Hervé
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supporting information
p. 2578 - 2585
(2021/03/18)
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- Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis
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The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH4)2S2O8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.
- Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
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supporting information
p. 2056 - 2060
(2019/03/13)
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- Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
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A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.
- Yang, Hui,Zheng, Wen-Hua
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p. 16177 - 16180
(2019/11/03)
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- Visible-light-triggered Catalytic Halohydrin Synthesis from Epoxides and Trichloroacetonitrile by Copper and Iron Salts
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Preparation of vicinal halohydrins, in which copper or iron chlorides catalyze the ring-opening reaction of epoxides with visible light effectively, is described. The use of trichloroacetonitrile as a halogen source enables catalytic HCl generation under the mild conditions. This method can also be applied to the aziridine ring-opening reaction.
- Toda, Yasunori,Tanaka, Katsumi,Matsuda, Riki,Suga, Hiroyuki
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supporting information
p. 1469 - 1471
(2019/12/02)
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- Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: Efficient synthesis of morpholines and 2-morpholones
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A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitrogen and oxygen sources, are successfully applied in the difunctionalization of conjugated dienes respectively. The majority of the desired products were obtained in moderate to excellent yields. Oxygen was successfully employed as a terminal oxidant. Further transformation of the generated products allowed for the expansion of structural diversity.
- Wen, Ke,Wu, Zhengxing,Chen, Buyun,Chen, Jianzhong,Zhang, Wanbin
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supporting information
p. 5618 - 5625
(2018/08/17)
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- A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines
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The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.
- Aubineau, Thomas,Cossy, Janine
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supporting information
p. 7419 - 7423
(2018/12/11)
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- Diastereoselective and Enantiospecific Synthesis of 1,3-Diamines via 2-Azaallyl Anion Benzylic Ring-Opening of Aziridines
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The 1,3-diamine motif appears in numerous complex molecules, yet there are few methods for the stereoselective construction of this moiety. Herein, we demonstrate a stereocontrolled synthesis of 1,3-diamines, which bear up to three contiguous stereogenic centers, through benzylic ring-opening of aziridines with 2-azaallyl anion nucleophiles. Reactions proceed efficiently (yield up to 95%), diastereoselectively (dr up to >20:1), site selectively, and enantiospecifically to deliver products with differentiated amino groups.
- Li, Kangnan,Weber, Alexandria E.,Tseng, Luke,Malcolmson, Steven J.
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p. 4239 - 4242
(2017/08/23)
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- Atmosphere- and Temperature-Controlled Regioselective Aminobromination of Olefins
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A complete switch of regioselectivity in the aminobromination of olefins is realized from delicate changes in the reaction temperature from 25 °C to 40 °C and the atmosphere from air to argon, under catalyst-free conditions. The resulting α-bromoamides ca
- Yu, Wesley Zongrong,Cheng, Yi An,Wong, Ming Wah,Yeung, Ying-Yeung
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supporting information
p. 234 - 239
(2017/02/05)
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- Thiyl radical-mediated cyclization of ω-alkynyl O-tert-butyldiphenylsilyloximes
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ω-Alkynyl O-tert-butyldiphenylsilyloximes, upon treatment with odorless 4-tert-butylbenzenethiol in the presence of azobisisobutyronitrile (AIBN) in refluxing benzene, underwent addition of a thiyl radical to the alkynyl group followed by radical cyclizat
- Shibata, Nina,Tsuchiya, Takahisa,Hashimoto, Yoshimitsu,Morita, Nobuyoshi,Ban, Shintaro,Tamura, Osamu
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supporting information
p. 3025 - 3034
(2017/04/10)
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- METHOD FOR PRODUCING COMPOUND HAVING 1,2-AMINO ALCOHOL SKELETON
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PROBLEM TO BE SOLVED: To provide a method for producing 1,2-amino alcohols that has a high regioselectivity and is safe and efficient. SOLUTION: Provided is a method for producing 1,2-amino alcohols represented by formula 3 below by letting an electrophil
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- Lewis acid mediated intramolecular C-O bond formation of alkanol-epoxide leading to substituted morpholine and 1,4-oxazepane derivatives: Total synthesis of (±)-Viloxazine
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Substituted morpholines have been efficiently synthesised in good yields from nitrogen tethered alkanol-epoxide mediated by boron trifluoride etherate. The methodology has been used for the total synthesis of (±)-viloxazine.
- Ghosh, Priya,Deka, Manash J.,Saikia, Anil K.
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p. 690 - 698
(2016/01/15)
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- Generation and Ring Opening of Aziridines in Telescoped Continuous Flow Processes
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A simple method for the preparation of a variety of N-sulfonyl aziridines (10 examples) from 1,2-amino alcohols under continuous flow conditions is described. Using flow based methods, the aziridines can be further ring opened with oxygen, carbon, and hal
- Hsueh, Nathanael,Clarkson, Guy J.,Shipman, Michael
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p. 3632 - 3635
(2015/07/28)
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- Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis
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A simple and regiospecific aminohydroxylation of olefins by photoredox catalysis has been developed. N-protected 1-aminopyridinium salts are the key compounds and serve as amidyl radical precursors by the action of Ir photocatalysts, fac-[Ir(ppy)3/s
- Miyazawa, Kazuki,Koike, Takashi,Akita, Munetaka
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p. 11677 - 11680
(2015/08/11)
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- Cis -1,2-Aminohydroxylation of Alkenes Involving a Catalytic Cycle of Osmium(III) and Osmium(V) Centers: OsV(O)(NHTs) Active Oxidant with a Macrocyclic Tetradentate Ligand
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Catalytic activity of [OsIII(OH)(H2O)(L-N4Me2)](PF6)2 (1: L-N4Me2 = N,N′-dimethyl-2,11-diaza-[3,3](2,6)pyridinophane) in 1,2-cis-aminohydroxylation of alkenes with sodium N-chloro-4-methylbenzenesulfonamide (chloramine-T) is explored. Simple alkenes as well as those containing several types of substituents are converted to the corresponding 1,2-aminoalcohols in modest to high yields. The aminoalcohol products have exclusively cis conformation with respect to the introduced -OH and -NHTs groups. The spectroscopic measurements including cold mass spectroscopic study of the reaction product of complex 1 and chloromine-T as well as density functional theory (DFT) calculations indicate that an oxido-aminato-osmium(V) species [OsV(O)(NHTs)(L-N4Me2)](PF6)2 (2) is an active oxidant for the aminohydroxylation. The DFT calculations further indicate that the reaction involves a [3 + 2] cycloaddition between 2 and alkene, and the regioselectivity in the aminohydroxylation of unsymmetrical alkenes is determined by the orientation that bears less steric hindrance from the tosylamino group, which leads to the energetically more preferred product isomer.
- Sugimoto, Hideki,Mikami, Akine,Kai, Kenichiro,Sajith,Shiota, Yoshihito,Yoshizawa, Kazunari,Asano, Kaori,Suzuki, Takeyuki,Itoh, Shinobu
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p. 7073 - 7082
(2015/08/03)
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- NaHSO3-Promoted ring openings of n-tosylaziridines and epoxides with H2O
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NaHSO3-oriented ring openings of a wide variety of N-tosylaziridines and epoxides with H2O under mild conditions in acetone was found to be a convenient and effective method, which provided the desired ss-aminoalcohols and ss-diols in good to excellent yields and with uniformly high regioselectivity.
- Li, Xing,Ni, Bin,Chang, Hong-Hong,Wei, Wen-Long
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p. 1009 - 1015
(2014/04/17)
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- Bromamine-T as an efficient amine source for Sharpless asymmetric aminohydroxylation of olefins
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Asymmetric aminohydroxylation of various olefins was carried out using bromamine-T as nitrogen source in the presence of (DHQ)2PHAL ligand. The new nitrogen source has been found to be effective in terms of yield and reaction time. The optical purities of the products could be obtained with up to 99% ee.
- Borah, Arun Jyoti,Phukan, Prodeep
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p. 713 - 715
(2014/01/23)
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- Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion
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An anti-Markovnikov geminal oxyamination of styrenyl alkenes in an intermolecular fashion using the umpolung strategy mediated by the bromonium ion is reported. Isotope labeling studies confirm the migration of the phenyl group in the semipinacol rearrang
- Balaji, Pandur Venkatesan,Chandrasekaran, Srinivasan
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supporting information
p. 70 - 72
(2014/01/06)
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- Defined hypervalent iodine(III) reagents incorporating transferable nitrogen groups: Nucleophilic amination through electrophilic activation
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Only I and N: Hypervalent iodine(III) reagents with two reactive I-N single bonds have been isolated for the first time. Their solid-state and solution structures provide evidence for enhanced electrophilicity at iodine and nucleophilic character of the imine. As a result, improved reactivity in amination reactions and unprecedented nitrogen-transfer reactions under metal-free conditions are realized. Copyright
- Souto, Jose A.,Martinez, Claudio,Velilla, Irene,Muniz, Kilian
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p. 1324 - 1328
(2013/03/13)
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- Efficient and regioselective ring-opening of arylaziridines with alcohols, thiols, amines and N-heteroaromatic compounds using sulphated zirconia
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Sulphated zirconia is an efficient catalyst for the regioselective ring-opening of aryl-substituted aziridines. This heterogeneous catalyst can be used several times without loss of activity and is compatible with a variety of acid sensitive and slightly basic nucleophiles.
- Llaveria, Josep,Espinoza, Araceli,Negrón, Guillermo,Isabel Matheu,Castillón, Sergio
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supporting information; experimental part
p. 2525 - 2529
(2012/06/18)
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- Ring-opening reaction of aziridines using aqueous polyacrylamide (PAM) as the reaction medium
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A novel efficient method for the hydrolysis of aziridines using aqueous Polyacrylamide (PAM) is described. An aqueous PAM solution serves as the reagent, the catalyst and the reaction medium. The reaction is fast (30 min), operationally simple, regiosclec
- Wang, Yan,Zhang, Ming Jie,Zhu, Jie,Li, Zhong Bo
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experimental part
p. 1367 - 1370
(2012/04/10)
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- Synthesis of optically active β-amino alcohols by asymmetric transfer hydrogenation of α-amino ketones
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A number of optically active amino alcohols were synthesized by direct asymmetric transfer hydrogenation of the corresponding amino ketones with good-to-high enantiomeric excesses (up to 95%) and excellent yields (up to 93%). When the range of substrates was broadened to include α-sulfonamido ketones or α-keto sulfones, the corresponding products were obtained with 100% enantiomeric excesses. The absolute configuration of (1R)-2-[(4- chlorophenyl) amino]-1-(4-methoxyphenyl) ethanol was confirmed by X-ray crystal structure analysis. Georg Thieme Verlag Stuttgart.
- Xu, Zhou,Zhu, Songlei,Liu, Yongmin,He, Ling,Geng, Zhicong,Zhang, Yawen
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experimental part
p. 811 - 817
(2010/10/01)
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- Facile synthesis of oxazolidinones catalyzed by n-Bu4NBr 3/n-Bu4NBr directly from olefins, chloramine-T and carbon dioxide
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A binary catalyst systemcomposed of n-Bu4NBr3/n-Bu4NBrwas developed for facile synthesis of 5-substituted 2-oxazolidinoneswith perfect regioselectivity in a single operation directly fromolefins, chloramine-T and CO2. The choice of efficient binary catalysts for two steps, i.e. aziridination and cycloaddition, and the optimization of reaction condition are keys to the one-pot synthesis of 5-substituted 2-oxazolidinones. A possiblemechanismfor the present one-pot synthesis of oxazolidinones was also proposed.
- Kong, De-Lin,He, Liang-Nian,Wang, Jin-Quan
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experimental part
p. 992 - 995
(2010/11/16)
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- Catalyst-free process for the synthesis of 5-aryl-2-oxazolidinones via cycloaddition reaction of aziridines and carbon dioxide
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A simple approach for facile synthesis of 5-aryl-2-oxazolidinones in excellent regioselectivity from aziridines under compressed CO2 conditions was developed in the absence of any catalyst and organic solvent. The reaction outcome was found to be tuned by subtly adjusting CO2 pressure. The adduct formed in situ of aziridine and CO2 is assumed to act as a catalyst in this reaction, which was also studied by means of in situ FT-IR technique.
- Dou, Xiao-Yong,He, Liang-Nian,Yang, Zhen-Zhen,Wang, Jing-Lun
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supporting information; experimental part
p. 2159 - 2163
(2010/10/21)
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- A straightforward synthesis of enantiopure 2,6-disubstituted morpholines by a regioselective O-protection/activation protocol
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Enantiopure 2,6-disubstituted morpholines have been synthesized through the ring opening of chiral, nonracemic oxiranes with nitrogen nucleophiles, under solid-liquid phase-transfer catalysis (SL-PTC) conditions. The β-hydroxytosyl amides resulting from the ring opening of a first epoxide with TsNH2 was used as nucleophile, after protection of the hydroxyl group, in the reaction with a second oxirane. The morpholine skeleton has been generated through standard functional group chemistry, followed by cyclization of the intermediate β-hydroxy-β′-tosyloxy-tosylamides carried out under SL-PTC conditions. N-Tosyl morpholines produced can be employed as building blocks in the synthesis of pharmaceuticals and as chiral tools. Georg Thieme Verlag Stuttgart.
- Penso, Michele,Lupi, Vittoria,Albanese, Domenico,Foschi, Francesca,Landini, Dario,Tagliabue, Aaron
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body text
p. 2451 - 2454
(2009/04/08)
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- Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles
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Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 °C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.
- Wang, Zhi,Cui, Yong-Tao,Xu, Zhao-Bing,Qu, Jin
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p. 2270 - 2274
(2008/09/19)
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- Osmium-catalyzed olefin dihydroxylation and aminohydroxylation in the second catalytic cycle
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Two catalytic cycles operate in the osmium-catalyzed olefin dihydroxylation and aminohydroxylation. Slow hydrolysis of the Os(VI) monoglycolate (or monoazaglycolate in aminohydroxylation) intermediate often results in the addition of another molecule of o
- Wu, Peng,Hilgraf, Robert,Fokin, Valery V.
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p. 1079 - 1085
(2007/10/03)
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- A mild and efficient procedure for the oxidation of epoxides and aziridines using cerium(IV) ammonium nitrate and NBS
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The CAN and NBS combination has been used for the first time for the synthesis of versatile α-hydroxy ketones and α-amino ketones from oxiranes/aziridines, respectively, in excellent yields. This method is a direct, one-pot, synthesis under mild conditions using acetonitrile-water (9:1) as solvent.
- Surendra,Srilakshmi Krishnaveni,Rama Rao
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p. 4111 - 4113
(2007/10/03)
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- A mild synthesis of13C-methanol
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The formation of oxazolidinon-2-ones from amino alcohols and carbon dioxide is well known. Until now it was not possible to reduce the fixed carbon dioxide to any basic chemical like formaldehyde or methanol, only the less interesting N-methyl compounds w
- Fr?hlich, J?rg,Berger, Stefan
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p. 2522 - 2524
(2007/10/03)
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- Synthesis of 2,6-disubstituted morpholines through regioselective oxiranes ring opening by tosylamide under PTC conditions
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Symmetric and non-symmetric 2,6-disubstituted morpholines were synthesized through regioselective nucleophilic ring opening of oxiranes with tosylamide under solid-liquid phase transfer catalysis (SL-PTC) conditions followed by cyclization of the tosylami
- Lupi, Vittoria,Albanese, Domenico,Landini, Dario,Scaletti, Davide,Penso, Michele
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p. 11709 - 11718
(2007/10/03)
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- Tetrabutylammonium bisulfate: A new effective catalyst for the hydrolysis of aziridines or epoxides
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Bu4NHSO4 (TBAHS) is an effective catalyst for the hydrolysis of aziridines and epoxides under mild and non-metal conditions to give the corresponding β-amino alcohols and 1,2-diols in high yields. The catalyst can be recycled.
- Fan, Ren-Hua,Hou, Xue-Long
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p. 1565 - 1567
(2007/10/03)
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- Highly regioselective ring opening of epoxides and aziridines using cerium(III) chloride
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A wide variety of epoxides and aziridines were converted to the corresponding β-halohydrins and β-haloamines using cerium(III) chloride and the cerium(III) chloride/NaI system in acetonitrile. The reactions were highly regioselective and efficient with excellent yields under mild and neutral reaction conditions.
- Sabitha, Gowravaram,Satheesh Babu,Rajkumar,Reddy,Yadav
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p. 3955 - 3958
(2007/10/03)
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- Synthesis of N-sulfonyl aziridines through regioselective opening of epoxides under solid-liquid PTC conditions
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The ring opening of epoxides 1 with 4-toluenesulfonamide (6) under solid-liquid phase transfer catalysis (SL-PTC) conditions afforded regioselectively β-sulfonamidoalcohols 7 in high yields. These were further convened into N-sulfonylaziridines 9 after ac
- Albanese, Domenico,Landini, Dario,Penso, Michele,Petricci, Silvia
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p. 6387 - 6394
(2007/10/03)
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- Nucleophilic ring opening of cyclic 1,2-sulfites with nitrogen nucleophiles. A route to enantiopure benzylic amino alcohols
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The reaction between cyclic 1,2-sulfites and two imide and two sulfonamide nucleophiles has been investigated in order to develop a procedure for the enantioselective preparation of N-protected vicinal amino alcohols. The results show that both imide and sulfonamide anions react with cyclic sulfites, yielding the desired products. In some cases the regioselectivities are low, and for the sulfonamides products originating from nucleophilic addition to the sulfite sulfur are observed. Acta Chemica Scandinavica 1998.
- Nymann, Kirsten,Mylvaganam, Saravanapavan,Svendsen, John S.
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p. 1060 - 1063
(2007/10/03)
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- Iodine-catalyzed aziridination of alkenes using chloramine-T as a nitrogen source
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Iodine was found to be an efficient catalyst for the aziridination of alkenes utilizing Chloramine-T (N-chloro-N-sodio-p-toluenesulfonamide) as a nitrogen source. For example, when two equivalents of styrene were added to Chloramine-T in the presence of a
- Ando, Takeya,Kano, Daisuke,Minakata, Satoshi,Ryu, Ilhyong,Komatsu, Mitsuo
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p. 13485 - 13494
(2007/10/03)
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- Baker's Yeast Reduction of α-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols
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Enzymatic reduction of α-acylaminoacetophenones with fermenting baker's yeast afforded optically active (R)-2-acylamino-1-arylethanols.Furthermore, lipase-catalyzed resolution of the 2-acylamino-1-arylethanols using vinyl acetate as an acyl donor resulted in the formation of (S)-1-acetoxy-2-acylamino-1-arylethanols and (R)-2-acylamino-1-arylethanols.
- Izumi, Taeko,Fukaya, Katsumi
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p. 1216 - 1221
(2007/10/02)
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