Asymmetric Domino Michael-Henry Reaction of 1,2-Diones with Nitroolefins Catalyzed by Chiral Ni(II) Complexes
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
Recommended Citation
Liang, Qian, "Asymmetric Domino Michael-Henry Reaction of 1,2-Diones with Nitroolefins Catalyzed by Chiral Ni(II) Complexes" (2015). Electronic Theses & Dissertations. 676.
https://digitalcommons.tamuc.edu/etd/676
