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通过对映体纯的N-丙烯酰基高烯丙基胺进行闭环复分解反应实现δ-取代的α,β-不饱和δ-内酰胺的不对称合成。

Asymmetric synthesis of delta-substituted alpha,beta-unsaturated delta-lactams by ring closing metathesis of enantiomerically pure N-acryloyl-homoallylic amines.

作者信息

Fiorelli Claudio, Savoia Diego

机构信息

Dipartimento di Chimica G. Ciamician, Università di Bologna, via Selmi 2, 40126 Bologna, Italy.

出版信息

J Org Chem. 2007 Aug 3;72(16):6022-8. doi: 10.1021/jo0703000. Epub 2007 Jul 11.

Abstract

Optically pure secondary homoallylic amines, obtained by highly diastereoselective addition of allylmetal reagents to imines derived from chiral amines, were N-dealkylated, and the primary amines were converted to N-acryloyl amides. Then, ring closing metathesis gave delta-substituted delta-lactams in good overall yields.

摘要

通过将烯丙基金属试剂与手性胺衍生的亚胺进行高度非对映选择性加成得到的光学纯仲高烯丙基胺进行N-脱烷基化反应,然后将伯胺转化为N-丙烯酰基酰胺。接着,闭环复分解反应以良好的总收率得到δ-取代的δ-内酰胺。

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