88335-95-9Relevant academic research and scientific papers
Enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides and 1,2-dicarboximides: Asymmetric synthesis of bicyclic lactones and hydroxylactams
Matsuki,Inoue,Ishida,Takeda,Nakagawa,Hino
, p. 9 - 18 (2007/10/02)
Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2- dicarboxylic anhydrides (1, 4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH4)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2- naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et3SiH) and trifluoroacetic acid (CF3CO2H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.
Simplified Chiral Aminolysis of Prochiral ?-Symmetric Dicarboxylic Anhydrides with Sodium Salt of 4(S)-IPTT
Nagao, Yoshimitsu,Hagiwara, Yuichi,Hasegawa, Yukari,Ochiai, Masahito,Inoue, Takehisa,et al.
, p. 381 - 384 (2007/10/02)
Highly enantioselective chiral aminolysis of cis-4-cyclohexen-1,2-ylenebis(carboxylic acid) anhydride has been performed by employing sodium salt of 4(R)-isopropyl-1,3-thiazolidine-2-thione in THF-DMSO.Other chiral aminolyses of prochiral ?-symmetric dicarboxylic anhydrides such as cis-cyclobutan-1,2-ylenebis(carboxylic acid) anhydride, meso-2,4-dimethylglutaric anhydride, and 3-glutaric anhydride were similarly investigated.
AN ASYMMETRIC SYNTHESIS OF BICYCLIC LACTONES AND ITS APPLICATION TO THE ASYMMETRIC SYNTHESIS OF (1R,3S)-CIS-CHRYSANTHEMIC ACID
Mukaiyama, Teruaki,Yamashita, Hiroyuki,Asami, Masatoshi
, p. 385 - 388 (2007/10/02)
Optically active bicyclic lactones are synthesized from imides, derived from (R)-(-)-2-amino-2-phenylethanol and meso-cyclic-1,2-cis-dicarboxylic acids, by successive treatment with sodium bis(2-methoxyethoxy)aluminum hydride and sodium borohydride, followed by acid hydrolysis.This reaction is successfully applied to the asymmetric synthesis of (1R,3S)-cis-chrysanthemic acid.
