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基于金鸡纳碱的双噁唑烷酮催化级联aza-Michael-Michael 加成:官能化螺[吲哚啉-3,3'-吡咯烷]四氢喹啉的对映选择性构建。

Cinchona-based squaramide-catalysed cascade aza-Michael-Michael addition: enantioselective construction of functionalized spirooxindole tetrahydroquinolines.

机构信息

School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China.

出版信息

Chem Commun (Camb). 2013 Oct 9;49(78):8842-4. doi: 10.1039/c3cc44930k.

Abstract

An efficient enantioselective cascade aza-Michael-Michael addition reaction catalysed by a chiral bifunctional tertiary amine-squaramide catalyst has been developed. This cascade reaction proceeded well under mild conditions, furnishing highly functionalized spirooxindole tetrahydroquinolines with three contiguous stereocenters in excellent yields with excellent diastereoselectivities (>25:1 dr) and high enantioselectivities (up to 94% ee).

摘要

一种高效的对映选择性级联氮杂迈克尔-迈克尔加成反应,由手性双功能叔胺-酰亚胺催化剂催化,已经被开发出来。该级联反应在温和的条件下进行得很好,以优异的产率、极好的非对映选择性(>25:1 dr)和高对映选择性(高达 94%ee),提供了高度官能化的螺环吲哚四氢喹啉,具有三个连续的立体中心。

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