Oxazaborolidine-catalysed reduction of alk-2-ene-1,4diones.: A convenient access to chiral 1,4-diols

被引：35

作者：

Bach, J ^{[1
]}

Berenguer, R ^{[1
]}

Garcia, J ^{[1
]}

López, M ^{[1
]}

Manzanal, J ^{[1
]}

Vilarrasa, J ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, Div 3, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 1998年 / 54卷 / 49期

关键词：

asymmetric synthesis; diols; oxazaborolidines; reduction;

D O I：

10.1016/S0040-4020(98)00936-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the preparation of C-2-symmetric, chiral alk-2-ene-1,4-diols (4) has been achieved, based on the borane-mediated reduction of symmetric alk-2-ene-1,4-diones (2) in the presence of oxazaborolidine (R)-1. In general, the presence of the double bond in 2 has been beneficial (compared with the related saturated 1,4-diketones 3) not only as far as the stereoselectivity in the reduction step is concerned, but also because it allowed us to remove meso-4 by chomatography and/or to improve the stereochemical purity of several resulting mixtures of diols 4 by Sharpless' epoxidation. Enantioenriched compounds 4 have been readily reduced to saturated diols with negligible loss of optical purity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：14947 / 14962

页数：16

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