Tetrahedron: Asymmetry

Preparation of highly enantiomerically pure linear secondary alcohols via asymmetric reduction of prochiral ketones with borane

J Xu, X Su, Q Zhang

Index: Xu, Jiaxi; Su, Xianbin; Zhang, Qihan Tetrahedron Asymmetry, 2003 , vol. 14, # 13 p. 1781 - 1786

Full Text: HTML

Citation Number: 35

Abstract

An efficient and practical preparation of homochiral linear secondary alcohols, 1-(4- alkylphenyl) and 1-(4-alkoxylphenyl) alcohols, via the asymmetric oxazaborolidine- catalyzed borane reduction of prochiral ketones is described. The phenomenon of the enantioselectivity of 1-(4-alkoxylphenyl) alcohols lower than that of 1-(4-alkylphenyl) alcohols was found and rationalized to the coordination of the oxygen atom in the alkoxy ...