2,5-DISUBSTITUTED PYRROLIDINES FROM D-MANNITOL-DERIVED BIS-AZIRIDINES

被引：27

作者：

FITREMANN, J ^{[1
]}

DUREAULT, A ^{[1
]}

DEPEZAY, JC ^{[1
]}

机构：

[1] UNIV PARIS 05,CNRS,CHIM & BIOCHIM PHARMACOL & TOXICOL LAB,F-75270 PARIS 06,FRANCE

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 08期

关键词：

D O I：

10.1016/0040-4039(94)88023-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Concise syntheses of 3, 4-dihydroxy-2,5-disubstituted pyrrolidines have been achieved starting from D-mannitol-derived flexible L-Ido bis-aziridines. Nucleophilic ring opening of the N-Boc and the N-Cbz activated bis-aziridines by phenylthiolate and azide ions has been studied; the reaction can be oriented either toward bis-opening (derivative A) or heterocyclization. Heterocyclization leads to a 1:9 mixture of the enantiopure polysubstituted piperidines B and pyrrolidines C.

引用

页码：1201 / 1204

页数：4

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