Asymmetric Synthesis of cis- and trans-2,5-disubstituted pyrrolidines from 3-oxo pyrrolidine 2-phosphonates:: Synthesis of (+)-preussin and analogs

被引：40

作者：

Davis, Franklin A. ^{[1
]}

Zhang, Junyi ^{[1
]}

Qiu, Hui ^{[1
]}

Wu, Yongzhong ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 07期

关键词：

D O I：

10.1021/ol800255r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrrolidine enones, derived from 3-oxo pyrrolidine 2-phosphonates and a HWE reaction with aldehydes, on Luche reduction give pyrrolidine allylic alcohols. The alcohols on hydrogenation (Pd/H(2)) give cis-2,5-disubstituted pyrroliclines and on treatment with TFA-NaBH(3)CN undergo a hydroxy directed reduction to trans-2,5-disubstituted pyrrolidines.

引用

页码：1433 / 1436

页数：4

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