Transition metal-catalyzed cross-coupling reactions have revolutionized the synthesis of natural products and medicinal agents and provided rapid synthetic access to a diverse range of molecules for biological testing. Important challenges remain, however, particularly in reactions that form C–C bonds between sp3 hybridized carbons. We are developing methods for stereospecific alkyl-alkyl cross coupling and cross-electrophile coupling reactions, where transposition of stereochemical information from the electrophilic starting material to the product occurs. Stereosepecific reductive coupling reactions for synthesis of cis- and trans-substituted cyclopropanes will be described. Application of these methods in synthesis of known bioactive compounds and in discovery of compounds that exhibit selective anti-cancer activity will also be reported.

Nickel-catalyzed stereospecific reductive cross-electrophile coupling reactions

254th National Meeting (2017)

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