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Title: Studies on the synthesis of Squaric Acid Ephedrine and their application in Asymmetric Catalytic Borane reduction of Prochiral Ketones
Authors: Lu, SM
Zhou, HB
Zhang, J
Xie, RG
Zhou, ZY
Chan, ASC
Yang, DK
Keywords: Asymmetric catalysis
Chiral oxazaborolidines
Reduction of aryl ketones
Squaric ephedrine amide
Issue Date: 2001
Publisher: 高等學校化學學報編輯部
Source: 高等学校化学学报 (Chemical journal of Chinese universities), 2001, v. 22, no. 11, p. 1850-1851 How to cite?
Journal: 高等学校化学学报 (Chemical journal of Chinese universities) 
Abstract: Seven squaric acid ester amides or squaric acid diamides have been conveniently prepared by the reaction of natural ephedrine and squaric acid diesters, in which the later can be sythesized by refluxing squaric acid in the corresponding alcohols. When squaric acid amide ester 4a reacted with alkyl amines or was treated with aqueous sodium hydrosulfide, the new ligands which contain nitrogen or sulfur atom at C-3 of squaric acid were obtained. Five ligands were synthesized for the first time. The chiral oxazaborolidines formed in situ have been used in the enantioselective borane reduction of prochiral ketones and diketones to afford the alcohols in the range 85%-98% yields and 52.5%-87.4% enantiomeric excess respectively. All new ligand structures were comfirmed by IR, 1H NMR, MS and elemental analysis, the crystal structure of compound 4b was lerrified by X-ray diffraction.
ISSN: 0251-0790
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