Stereospecific nickel-catalyzed cross-coupling reactions of enantioenriched benzylic alcohol derivatives have been developed. Kumada-type cross-coupling of benzylic ethers with aryl Grignard reagents proceeds with inversion of stereochemistry at the reactive center. Cross-coupling of benzylic carbamates with boronic esters proceeds with either retention or inversion of stereochemistry, as determined by the choice of achiral catalyst. These methods have been applied to the synthesis of enantioenriched triarylmethanes. Cascade sequences utilizing our stereospecific cross-coupling methodology will also be discussed.

Development of stereospecific nickel-catalyzed cross-coupling reactions of benzylic alcohol derivatives

247th National Meeting (2014)

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