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

作者:Guo Yi An; Liang Tao; Kim Seung Wook; Xiao Hongde; Krische Michael J*
来源:Journal of the American Chemical Society, 2017, 139(20): 6847-6850.
DOI:10.1021/jacs.7b03371

摘要

Under the conditions of nickel(0) catalysis, enantiomerically enriched vinyl dioxanones engage boroxines or B-2(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.

  • 出版日期2017-5-24