Nickel-Catalyzed Cross-Coupling of Vinyl Dioxanones to Form Enantiomerically Enriched Cyclopropanes.

ABSTRACT: Under the conditions of nickel(0) catalysis, enantiomerically enriched vinyl dioxanones engage boroxines or B₂(pin)₂ in stereospecific cross-coupling to form diverse tetrasubstituted cyclopropanes bearing all-carbon quaternary stereocenters. The collective data corroborate a mechanism involving nickel(0)-mediated benzylic oxidative addition with inversion of stereochemistry followed by reversible olefin insertion to form a (cyclopropylcarbinyl)nickel complex, which upon reductive elimination releases the cyclopropane.

SUBMITTER: Guo YA 

PROVIDER: S-EPMC5651680 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature