路易斯酸催化的 N-对甲苯磺酰基氮杂环丙烷与富电子烯烃的[3+2]环加成反应通过选择性碳-碳键断裂实现。

Lewis acid-catalyzed formal [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage.

机构信息

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, China.

出版信息

Chem Commun (Camb). 2011 May 7;47(17):5049-51. doi: 10.1039/c1cc10926j. Epub 2011 Mar 24.

DOI:10.1039/c1cc10926j

PMID:21437311

Abstract

A novel, mild, robust catalyst Y(OTf)(3) for C-C bond heterolysis of N-tosyl aziridines was developed and the resulting metallo-azomethine ylides may readily undergo [3+2] dipolar cycloaddition with an electron-rich olefin via a stepwise reaction pathway with high regio- and diastereoselectivity leading to substituted pyrrolidines.

摘要

开发了一种新型、温和、稳定的催化剂 Y(OTf)(3)，用于 N-对甲苯磺酰基氮杂环丙烷的 C-C 键异裂，所得的金属氮宾叶立德可以通过逐步反应途径与富电子烯烃容易地发生[3+2]偶极环加成反应，具有高区域和立体选择性，得到取代的吡咯烷。