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

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• 作者：Stephen W. Wright ; Chulho Choi ; Seungwon Chung ; Brian P. Boscoe ; Susan E. Drozda ; James J. Mousseau ; John D. Trzupek
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：17
• 期：21
• 页码：5204-5207
• 全文大小：264K
• ISSN：1523-7052

文摘

We report that the stereochemical outcome of the conjugate addition of organocopper reagents to bicyclic 伪,尾-unsaturated lactams derived from pyroglutaminol is determined by the nature of the aminal group. Bicyclic 伪,尾-unsaturated lactams in which the aminal is derived from a ketone have been found to afford products of syn conjugate addition. By contrast, bicyclic 伪,尾-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.