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N-杂环卡宾催化β-甲基烯醛与环状三氟甲基酮亚胺的[4+2]环化反应用于二氢喹唑啉酮衍生物的不对称合成

N-Heterocyclic carbene-catalyzed [4+2] annulation of β-methyl enals and cyclic trifluoromethyl ketimines for the asymmetric synthesis of dihydroquinazolinone derivatives.

作者信息

Liu Qiang, Chen Xiang-Yu, Li Sun, Jafari Ehsan, Raabe Gerhard, Enders Dieter

机构信息

Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany.

出版信息

Chem Commun (Camb). 2017 Oct 12;53(82):11342-11344. doi: 10.1039/c7cc06562k.

Abstract

The enantioselective oxidative N-heterocyclic carbene-catalyzed [4+2] annulation reaction of β-methyl enals and cyclic trifluoromethyl ketimines has been developed. A series of biologically interesting dihydroquinazolinone derivatives bearing a trifluoromethyl group and a tetrasubstituted stereocenter are efficiently prepared with very good yields and excellent stereoselectivities.

摘要

已开发出对映选择性氧化氮杂环卡宾催化的β-甲基烯醛与环状三氟甲基酮亚胺的[4+2]环化反应。一系列具有三氟甲基和四取代立体中心的具有生物学意义的二氢喹唑啉酮衍生物得以高效制备,产率很高且立体选择性优异。

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