A chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction through a kinetic resolution of MBH alcohols: highly enantioselective synthesis of three-dimensional heterocyclic compounds

Leijie Zhou; Yuan Zeng; Xing Gao; Qijun Wang; Chang Wang; Bo Wang; Wei Wang; Yongjun Wu; Bing Zheng; Hongchao Guo

doi:10.1039/C9CC05483A

A chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction through a kinetic resolution of MBH alcohols: highly enantioselective synthesis of three-dimensional heterocyclic compounds†

Leijie Zhou,^a Yuan Zeng,^a Xing Gao,

^a Qijun Wang,^a Chang Wang,^a Bo Wang,^a Wei Wang,^b Yongjun Wu,^b Bing Zheng*^a and Hongchao Guo

*^a

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* Corresponding authors

^a Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
E-mail: hchguo@cau.edu.cn, 2014026@cau.edu.cn

^b College of Public Health, Zhengzhou University, Zhengzhou 450001, China

Abstract

In this communication, a chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction of unmodified Morita–Baylis–Hillman alcohols with azomethine imines has been achieved through a kinetic resolution of MBH alcohols under mild conditions, giving pharmaceutically interesting functionalized hetero-bicyclo[3.3.1]nonane derivatives in good to excellent yields with excellent enantioselectivities.

Chemical Communications

A chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction through a kinetic resolution of MBH alcohols: highly enantioselective synthesis of three-dimensional heterocyclic compounds†

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A chiral squaramide-catalyzed asymmetric dearomative tandem annulation reaction through a kinetic resolution of MBH alcohols: highly enantioselective synthesis of three-dimensional heterocyclic compounds

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