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, where transposition of stereochemical information from the electrophilic starting material to the product occurs. Cross-coupling reactions typically occur with inversion at the reactive center. Stereodivergent reactions, where choice of achiral ligand determines whether the reaction occurs with retention or inversion, will also be presented. 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 cross-coupling and reductive coupling reactions

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.