Transition metal catalyzed reactions of electrophilic intermediates to form C-C bonds and set stereogenic centers
Date
2015
Authors
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Publisher
University of Delaware
Abstract
(1) The first project I have worked on is titled Nickel Catalyzed Cyclization of N-Benzoylaminals for Isoindolinone Synthesis. My studies demonstrated the functional group tolerance and contributed strongly to our mechanistic understanding of this cyclization reaction. These results were published in Organic Letters in 2011. (2) The second project I have worked on is titled Enantioselective, Copper(I)-Catalyzed Alkynylation of Oxocarbenium Ions to Set alpha,alpha-diaryl Tetrasubstituted Stereocenters. In summary, I have developed the first example of an enantioselective addition of alkynes to a cyclic oxocarbenium ion to set tetrasubstituted stereocenters. The success of this reaction relied on identification of a Cu/PyBox catalyst, along with CHCl3 as solvent, BF3 ̇OEt2 as Lewis acid, and MTBD as base. Under the optimized conditions, a variety of ketals and alkynes underwent the reaction in good to excellent yields and enantioselectivites. These results have been published in Angewandte Chemie International Edition, ASAPs. (3) The third project I have worked on is titled Enantioselective, Copper(I)-Catalyzed Alkynylation of Iminium Ions to Set alpha,alpha-diaryl, Tetrasubstituted Stereocenters. Here I have demonstrated the first example of enantioselective addition of alkynes to cyclic iminium ions to set diaryl tetrasubstituted stereocenters. These results are ready to be published in the fall of 2015.