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
收藏
页码：1433 / 1436
页数：4
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