3 years ago

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

Nickel-Catalyzed Cross-Coupling of Vinyl Dioxanones to Form Enantiomerically Enriched Cyclopropanes
Yi-An Guo, Tao Liang, Hongde Xiao, Michael J. Krische, Seung Wook Kim
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b03371

DOI: 10.1021/jacs.7b03371

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