Diastereo- and enantioselective synthesis of 4,5,6-trisubstituted and 6-monosubstituted piperidin-2-ones

被引：0

作者：

Enders, D

Bartzen, D

机构：

来源：

LIEBIGS ANNALEN-RECUEIL | 1997年 / 06期

关键词：

4,5,6-Tri- and 6-monosubstituted piperidin-2-ones; SAMP/RAMP hydrazone method; Michael additions; alkylative aldehyde amination; lactams;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient, versatile and highly diastereo- and enantioselective synthesis of 4,5,6-trisubstituted piperidin-2-ones 1 in satisfactory overall yields is described. The procedure involves the efficient and highly anti-diastereo- and enantioselective Michael addition of aldehydes to enoates via their lithiated SAMP hydrazones, followed by nucleophilic 1,2-addition of organometallic reagents to the C=N double bond of the corresponding aldehyde SAMP hydrazone-lithium ester enolate and subsequent lactamisation. In addition, 6-monosubstituted piperidin-2-ones 8 are prepared with enantiomeric excesses of ee = 79-92% via a similar three-step sequence starting from ethyl 5-oxovalerate (9).

引用

页码：1115 / 1123

页数：9

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