用于合成吡咯烷的催化三组分组装反应。

Catalytic, three-component assembly reaction for the synthesis of pyrrolidines.

作者信息

Galliford Chris V, Beenen Melissa A, Nguyen SonBinh T, Scheidt Karl A

机构信息

Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.

出版信息

Org Lett. 2003 Sep 18;5(19):3487-90. doi: 10.1021/ol035292y.

DOI:10.1021/ol035292y

PMID:12967306

Abstract

[reaction: see text] Copper(I) salts catalyze the three-component assembly reaction between an alpha-diazo ester, an imine, and various alkenes and alkynes to form substituted pyrrolidines with excellent to good diastereoselectivities in high yields. The transition metal-catalyzed decomposition of the alpha-diazo compound in the presence of the imine likely generates a transient azomethine ylid that undergoes addition with various dipolarophiles in a highly convergent manner.

摘要

[反应：见正文] 铜（I）盐催化α-重氮酯、亚胺与各种烯烃和炔烃之间的三组分组装反应，以高收率形成具有优异至良好非对映选择性的取代吡咯烷。在亚胺存在下，过渡金属催化的α-重氮化合物分解可能产生瞬态甲亚胺叶立德，其以高度汇聚的方式与各种亲偶极体发生加成反应。