Enantioselective synthesis of (S)-Vigabatrin(R)

被引：37

作者：

Alcon, M ^{[1
]}

Poch, M ^{[1
]}

Moyano, A ^{[1
]}

Pericas, MA ^{[1
]}

Riera, A ^{[1
]}

机构：

[1] UNIV BARCELONA,DEPT QUIM ORGAN,URSA,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(97)00346-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An asymmetric synthesis of fully protected (S)-Vigabatrin(R) has been developed. The key intermediate in the sequence is enantiomerically pure N-Boc-5-phenyl-3-amino-1,2-diol 5a, obtained from (E)-5-phenyl-2-penten-1-ol by employing a catalytic Sharpless epoxidation as the sole source of chirality. Aminodiol 50 was converted into the target N-Boc-(S)-Vigabatrin methyl ester 3 by a five-step sequence involving the actualization of the latent carboxyl group (phenyl oxidation) and a Corey-Hopkins deoxygenative protocol of the 1,2-diol. (C) 1997 Elsevier Science Ltd.

引用

页码：2967 / 2974

页数：8

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