N-杂环卡宾催化的立体选择性串联反应：官能化四氢喹啉的合成。

N-heterocyclic carbene-catalyzed stereoselective cascade reaction: synthesis of functionalized tetrahydroquinolines.

机构信息

State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.

出版信息

Org Lett. 2013 Sep 20;15(18):4750-3. doi: 10.1021/ol4024985. Epub 2013 Sep 10.

PMID:24020617

Abstract

The first N-heterocyclic carbene-catalyzed stereoselective aza-Michael-Michael-lactonization cascade reaction of 2'-aminophenylenones and 2-bromoenals for the construction of chiral functionalized tetrahydroquinolines with three consecutive stereogenic centers has been achieved in high yields (up to 98%) with excellent diastereo- (>25:1) and enantioselectivities (up to 98.7% ee).

摘要

首例 N-杂环卡宾催化的 2'-氨基苯乙酮和 2-溴丙烯醛的立体选择性aza-Michael-Michael-内酯化级联反应，用于构建具有三个连续手性中心的手性功能化四氢喹啉，产率高达 98%（高达 98.7%ee），具有优异的非对映选择性（>25:1）和对映选择性。