Reversal of Diastereoselection in the Conjugate Addition of Cuprates to Unsaturated Lactams

被引：18

作者：

Wright, Stephen W. ^{[1
]}

Choi, Chulho ^{[1
]}

Chung, Seungwon ^{[1
]}

Boscoe, Brian P. ^{[1
]}

Drozda, Susan E. ^{[1
]}

Mousseau, James J. ^{[1
]}

Trzupele, John D. ^{[2
]}

机构：

[1] Pfizer Global Res & Dev, Worldwide Med Chem, Groton, CT 06340 USA

[2] Pfizer Global Res & Dev, Inflammat & Immunol Res, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 21期

关键词：

STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; PYROGLUTAMIC ACID; REAGENTS;

D O I：

10.1021/acs.orglett.5b02533

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report that the stereochemical outcome of the conjugate addition of organocopper reagents to bicyclic alpha,beta-unsaturated lactams derived from pyroglutaminol is determined by the nature of the aminal group. Bicyclic alpha,beta-unsaturated lactams in which the aminal is derived from a ketone have been found to afford products of syn conjugate addition. By contrast, bicyclic alpha,beta-unsaturated lactams in which the aminal is derived from an aldehyde afford products of anti conjugate addition. These remarkably different results obtained from very similar starting materials are unexpected.

引用

页码：5204 / 5207

页数：4

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