Jump to main content
Jump to site search

Issue 24, 2012
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Supplementary files

Article information


Submitted
18 Jan 2012
Accepted
17 Apr 2012
First published
17 Apr 2012

Org. Biomol. Chem., 2012,10, 4767-4773
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements