ChemInform Abstract: Nonracemic Allylic Boronates Through Enantiotopic‐Group‐Selective Cross‐Coupling of Geminal Bis(boronates) and Vinyl Halides.

Abstract

Nonracemic Allylic Boronates Through Enantiotopic-Group-Selective Cross--Coupling of Geminal Bis(boronates) and Vinyl Halides. -Under the influence of a chiral palladium catalyst, 1,1-bis(pinacolboronate) esters undergo asymmetric cross-coupling with bromoalkenes to generate nonracemic allyl boronates with high levels of enantioselectivity. Resulting allyl boronates can be used for further transformations. Mechanistic experiments suggest a pathway involving outer-sphere stereoinvertive transmetalation. -(POTTER, B.; SZYMANIAK, A. A.; EDELSTEIN, E. K.; MORKEN*, J. P.; J. Am. Chem. Soc. 136 (2014) 52, 17918-17921, http://dx.