ASYMMETRIC-SYNTHESIS OF 3S,4R-DIHYDROXYPYRROLIDINES BY REGIOSELECTIVE AND STEREOSELECTIVE HYDROXYLATION OF 4-OXOPROLINE ENOLATE

被引：31

作者：

BLANCO, MJ ^{[1
]}

SARDINA, FJ ^{[1
]}

机构：

[1] UNIV SANTIAGO DE COMPOSTELA,DEPT QUIM ORGAN,E-15706 SANTIAGO,SPAIN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(00)74441-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short, efficient and stereoselective synthesis of enantiomerically pure (2R, 3S, 4R) 3,4-dihydroxy-2-hydroxymethylpyrrolidine, a galactosidase inhibitor, from 4-hydroxy-L-proline is presented. The key steps are the regio- and stereoselective hydroxylation of a 4-oxoproline enolate and the stereoselective reduction of the resulting ketoalcohol. An N-(9-phenylfluoren-9-yl) moiety is used not only as an N-protecting group but as a regio- and stereochemical control element as well.

引用

页码：8493 / 8496

页数：4

共 32 条

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