双功能醋酸银催化的甲亚胺叶立德的不对称[3 + 2]环加成反应

Bifunctional AgOAc-catalyzed asymmetric [3 + 2] cycloaddition of azomethine ylides.

作者信息

Zeng Wei, Zhou Yong-Gui

机构信息

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian.

出版信息

Org Lett. 2005 Oct 27;7(22):5055-8. doi: 10.1021/ol0520370.

DOI:10.1021/ol0520370

PMID:16235956

Abstract

[reaction: see text] A bifunctional AgOAc-catalyzed asymmetric cycloaddition of azomethine ylides with electronic-deficient alkenes was developed using ferrocenyloxazoline-derived N,P ligands. The reactive metal-bound azomethine ylide dipole is formed by the deprotonation with acetate, and extra base is not necessary. The reactions proceed with high enantioselectivity. This method provides an efficient and convenient route to optically active pyrrolidine derivatives.

摘要

[反应：见正文] 使用二茂铁基恶唑啉衍生的N，P配体，开发了一种双功能醋酸银催化的缺电子烯烃与甲亚胺叶立德的不对称环加成反应。活性金属结合的甲亚胺叶立德偶极是通过用乙酸盐去质子化形成的，无需额外的碱。反应以高对映选择性进行。该方法为制备光学活性吡咯烷衍生物提供了一条高效便捷的途径。