Chiral bicyclic lactams as homoenolate equivalents: An asymmetric route to 5-substituted cyclohexenones

被引：28

作者：

Schwarz, JB ^{[1
]}

Devine, PN ^{[1
]}

Meyers, AI ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

TETRAHEDRON | 1997年 / 53卷 / 26期

关键词：

D O I：

10.1016/S0040-4020(97)90391-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclic Lactam 2 was transformed into alpha-cyanoenamine 8 in a four-step, high-yielding process. gamma-Metalation of 8 was achieved using LiTMP in THF/HMPA, and the resultant homoenolate equivalent underwent stereoselective alkylation and subsequent hydrolysis to provide lactams of type 10 as a single diastereomer. Partial reduction and hydrolysis of lactams 10 furnished enantiopure 5-substituted cyclohexenones 13 in good overall yield. (C) 1997 Elsevier Science Ltd.

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页码：8795 / 8806

页数：12

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