New approach to the preparation of bicyclo octane derivatives via the enantioselective cascade reaction catalyzed by chiral diamine-Ni(OAc)2 complex

Wenyi Li; Xiaodong Liu; Zhifeng Mao; Qiao Chen; Rui Wang

doi:10.1039/C2OB25135C

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New approach to the preparation of bicyclo octane derivatives via the enantioselective cascade reaction catalyzed by chiral diamine-Ni(OAc)₂ complex†

Wenyi Li,‡^a Xiaodong Liu,‡^a Zhifeng Mao,^a Qiao Chen^a and Rui Wang*^a

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* Corresponding authors

^a Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Science, Institute of Biochemistry and Molecular Biology School of Life Science, Lanzhou University, Lanzhou 730000, China
E-mail: wangrui@lzu.edu.cn
Fax: (+86) 931-891-2567

Abstract

A highly efficient catalyst system assembled from enantiomerically pure diaminocyclohexane and Ni(OAc)₂ is, for the first time, used to catalyze the cascade Michael–Henry reaction of various diones and substituted nitroalkenes. A series of polyfunctionalized bicyclo[3.2.1]octane derivatives containing four stereogenic centers are prepared with excellent enantioselectivities (up to >99% ee) and diastereoselectivities (up to 50 : 1 dr) with high yields. In addition, via this chiral diamine-Ni(OAc)₂ catalyst system, the base-induced epimerization leading to the decrease of stereoselectivity can be prevented.

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Article information

DOI: https://doi.org/10.1039/C2OB25135C
Article type: Paper
Submitted: 18 Jan 2012
Accepted: 17 Apr 2012
First published: 17 Apr 2012

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Org. Biomol. Chem., 2012,10, 4767-4773

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New approach to the preparation of bicyclo octane derivatives via the enantioselective cascade reaction catalyzed by chiral diamine-Ni(OAc)₂ complex

W. Li, X. Liu, Z. Mao, Q. Chen and R. Wang, Org. Biomol. Chem., 2012, 10, 4767 DOI: 10.1039/C2OB25135C

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Organic & Biomolecular Chemistry