- N -Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/br?nsted acid Co-catalyzed allylic C-H oxidation
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A Pd(II)/bis-sulfoxide/Br?nsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and π-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.
- Osberger, Thomas J.,White, M. Christina
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p. 11176 - 11181
(2014/08/18)
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- Highly stereoselective intramolecular SN2′ cyclization yielding chiral oxazolidin-2-ones: General route to α-hydroxy-β-amino acids
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Intramolecular nucleophilic attack onto allylsulfonates promoted by silica gel acting as an acid catalyst provides expedient stereoselective access to 4,5-difunctionalized oxazolidin-2-ones. Precursors were prepared efficiently from enantiopure α-amino ac
- Seo, Woo Duck,Curtis-Long, Marcus J.,Kim, Jin Hyo,Park, Jong Keun,Park, Ki Min,Park, Ki Hun
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p. 2289 - 2292
(2007/10/03)
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- PROCESSES FOR PRODUCING OXAZOLIDINONE DERIVATIVE OF BETA-HYDROXYETHYLAMINE COMPOUND AND FOR PRODUCING BETA-HYDROXYETHYLAMINE COMPOUND
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The present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the β-position to prepare oxazolidinone derivatives of β-hydroxyethylamine compounds having an inverted steric configuration at the β
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- PROCESS FOR PRODUCING 3-AMINO-2-HYDROXYPROPIONIC ACID DERIVATIVES
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The present invention provides a process for preparing 3-amino-2-hydroxypropionic acid derivatives (1) which does not use dangerous reagents, is economically advantageous, and is suitable for an industrial production, which process comprises:treating N-protected-3-amino-2-hydroxypropionic acid derivatives (2) having a steric configuration at 2-position carbon reverse to that of derivatives (1) with a leaving group-introducing agent to convert into N-protected-3-aminopropionic acid derivatives (3),then treating the derivatives with a basic substance to convert into substituted-3-amino-2-hydroxypropionic acid derivatives (4) having an inverted steric configuration at 2-position carbon,and then converting the derivatives into 3-amino-2-hydroxypropionic acid derivatives (1).
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- Process for producing norstatin derivatives
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This invention to provide a process for producing an optically active threo-phenylnorstatin derivative which does not require a toxic cyanating agent or a costly reagent, or a complicated procedure, and can be practiced on a commercial scale. This inventi
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- Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: A route to enantiopure β-amino-α-hydroxy acids
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Chiral α-dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-β-dibenzylamino-α-hydroxycyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure β-amino-α-hydroxy acids.
- Andres, Jose M.,Martinez, Maria A.,Pedrosa, Rafael,Perez-Encabo, Alfonso
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p. 347 - 353
(2007/10/03)
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- Process for producing optically active cyanohydrins
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An optically active cyanohydrin represented by the following general formula (1): STR1 wherein each of R1 and R2 is a hydrogen atom or an amino-protecting group, and the configurations relating to the carbon atoms at the *2-position and *3-position are as
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- Diastereoselective Synthesis of 3-Amino-2-Hydroxyalkanoic Acid Derivatives
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Both diastereomers of 3-amino-2-hydroxyalkanoic acid derivatives were synthesized selectively by LDA-induced reaction of N-methoxycarbonyl-1-methoxyamines with O-protected N,N-dimethylglycolamides.The inversion of the diastereoselectivity was highly achieved by 1) selecting the O-protecting groups and 2) the addition of Ti(OPr-i)4.
- Kise, Naoki,Inakoshi, Naoto,Matsumura, Yoshihiro
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p. 909 - 912
(2007/10/02)
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