Title

Asymmetric Domino Michael-Henry Reaction of 1,2-Diones with Nitroolefins Catalyzed by Chiral Ni(II) Complexes

Author

Qian Liang

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Spring 2015

Abstract

In this thesis, bisoxazolidine and ionic liquid supported chiral cyclohexane diamine -Ni(II) complexes have been developed for the first time to catalyze asymmetric Michael-Henry reaction of 1,2-cyclohexadione with various nitroolefins to give series of highly functional [3,2,1]bicyclo octane derivatives with high stereoselectivity and diastereoselectivity. Successful introduction of the ammonium groups into chiral cyclohexane diamine ligand has improved the reactivity and recyclability of the catalyst. Products of [3,2,1]bicyclo octane derivatives with four stereogenic centers formed in one step can be achieved in high yield (76~99%) with excellent enantioselectivities (76~99%) and high diastereoselectivities (up to 47:1).

Advisor

Bukuo Ni

Subject Categories

Chemistry | Physical Sciences and Mathematics

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