Substituent effects on the selectivity of catalytic asymmetric carbon-hydrogen activation and cyclopropanation transformations
Coleman, Michael Girard
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The impetus of the work reported herein was the exploration of rhodium(II) catalyzed decomposition of donor/acceptor carbenoids in the presence of tri-substituted and trans di-substituted alkenes. The goal of this project was to determine what role did the steric and electronic effects of the alkene had on the reactivity of the donor-acceptor carbenoid transformations. Moreover, Rh 2 (O 2 CCPh 3 ) 4 exhibited remarkable catalyst control over the chemoselectivity of C-H activation and cyclopropanation transformations. It was further utilized to improve the chemoselectivity of other cis disubstituted alkenes. The second part of this manuscript described the synthesis of a small library of 3-hydroxypyrrolidinols. These small molecules were tested for biological affinity. The ultimate goal of this work would act to identify lead compounds for the treatment of cocaine addiction.