Synthesis of enantiomerically pure 4-substituted pyrrolidin-3-ols via asymmetric 1,3-dipolar cycloaddition

被引：33

作者：

Karlsson, S ^{[1
]}

Högberg, HE ^{[1
]}

机构：

[1] Mid Sweden Univ, Dept Nat & Environm Sci, SE-85170 Sundsvall, Sweden

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(01)00367-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric 1,3-dipolar cycloadditions of chiral azomethine ylides to 3-benzyloxy-substituted alkenoyleamphorsultams are described. trans-3,4-Disubstituted pyrrolidines containing a protected hydroxyl group at C(4) of the pyrrolidine ring are obtained in high diastereomeric ratios. Such compound can serve as chiral building blocks for the syntheses of enantiopure bioactive pyrrolidines. This is exemplified by a short synthetic route to a known glycosidase inhibitor, (3R,4R)-4-(hydroxy- methyl)pyrrolidin-3-ol and its enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1977 / 1982

页数：6

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