26735-95-5Relevant articles and documents
Construction of acyclic all-carbon quaternary stereocenter based on asymmetric michael addition of chiral amine
Niki, Aya,Ozeki, Minoru,Kuse, Akiko,Nakagawa, Shiho,Aoki, Shui,Shigeta, Takashi,Kajimoto, Tetsuya,Iwasaki, Hiroki,Kojima, Naoto,Arimitsu, Kenji,Hosoi, Shinzo,Node, Manabu,Yamashita, Masayuki,Kawasaki, Ikuo
, p. 926 - 930 (2021/09/06)
Acyclic asymmetric quaternary stereocenters, which are composed of four carbon-carbon bonds, were finely constructed by utilizing a face-selective alkylation of enolate intermediates derived from an asymmetric Michael addition reaction of a chiral lithium amide with trisubstituted (E)-α,β-unsaturated esters. The present face-selective alkylation was able to employ diverse alkyl halides as an electrophile to afford various Michael adducts having an all-carbon quaternary stereocenter. With regard to the deprotection of the chiral auxiliary, N-iodosuccinimide used in our previous study did not work in the present cases; however, we found that pyridine iodine monochloride in the presence of H2O was effective to remove the bornyl group and the benzyl group on the amino group to provide the β-amino ester derivative.
A facile and convenient synthesis of trisubstituted (E)-α,β-unsaturated esters by tandem acetylation-E1CB reaction
Ozeki, Minoru,Hachino, Ayumi,Shigeta, Takashi,Niki, Aya,Kobayashi, Natsuko,Mizutani, Hideki,Nakamura, Akihiro,Horie, Ayano,Arimitsu, Kenji,Kajimoto, Tetsuya,Hosoi, Shinzo,Iwasaki, Hiroki,Kojima, Naoto,Yamashita, Masayuki,Kawasaki, Ikuo
, p. 71 - 74 (2019/01/17)
A facile and convenient synthesis of trisubstituted (E)-α,β-unsaturated esters was developed by improving our previously established method. The new method circumvented the separation of the intermediates, which have an activating group of the hydroxyl group in β-hydroxy esters, furnishing α,β-unsaturated esters in shorter steps than the previous method: an acetylation of β-hydroxy group and subsequent E1cB reaction proceeded in tandem. In addition, the new method can not only employ a diastereomeric mixture of the substrate for the E1cB reaction, it has a wide substrate scope as well, which would enable the synthesis of various trisubstituted (E)-α,β-unsaturated esters.
Lewis Acid Catalysis in Supercritical Carbon Dioxide. Use of Poly(ethylene glycol) Derivatives and Perfluoroalkylbenzenes As Surfactant Molecules Which Enable Efficient Catalysis in ScCO2
Komoto, Ichiro,Kobayashi, Shu
, p. 680 - 688 (2007/10/03)
Lewis acid catalysis in supercritical carbon dioxide (CO2) was investigated. While solubility of most organic materials is low in scCO 2, poly(ethylene glycol) derivatives or perfluoroalkylbenzenes were found to work as surfactants to dissolve organic materials in scCO2. In the presence of these molecules, Lewis acid catalyzed organic reactions such as aldol-, Mannich-, and Friedel-Crafts-type reactions proceeded smoothly in scCO2. Formation of emulsions was observed in these reactions, and the systems were studied in detail.