Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/9413
Title: Study on the synthesis of new chiral derivatives of squaric acid and their application in asymmetric catalytic borane reduction of prochiral aryl ketones
Authors: Lu, SM
Zhou, HB
Xie, RG
Zhou, ZY
Chan, ASC
Yang, TK
Keywords: Asymmetric catalysis
Chiral oxazaborolidine
Chiral squaric acid amidoalcohols
Reduction of aryl ketones
Issue Date: 2001
Publisher: 科學出版社
Source: 化学学报 (Acta chimica sinica), 2001, v. 59, no. 4, p. 587-593 How to cite?
Journal: 化学学报 (Acta chimica sinica) 
Abstract: Eleven new chiral squaric acid amidoalcohols bave been synthesized by reaction of alkyl amines or thiols with 3 - butoxy - [ (1′S, 2′R) - (2′ - hydroxy - 1′, 2′ - diphenylethyl)amino] - 3 - cyclobutene - 1, 2 - dione, which is prepared by the reaction of (1R, 2S) - 2 - amino - 1, 2 -diphenylalcohol with dibutyl squrate. The in situ formed chiral oxazaborolidines have been used in the enantioselective borane reduction of prochiral ketones to afford the alcohol products in a range 88% - 98% yield and 42% - 81% enantiomeric excesses, respectively. All of the new compounds are confirmed by IR, 1H NMR, MS and element analysis, in which compound 4b is also confirmed by X - ray analysis.
URI: http://hdl.handle.net/10397/9413
ISSN: 0567-7351
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