Journal of the American Chemical Society, Vol.137, No.35, 11262-11265, 2015
Synthesis of Adjacent Quaternary Stereocenters by Catalytic Asymmetric Allylboration
Allylboration of ketones with gamma-disubstituted allylboronic acids is performed in the presence of chiral BINOL derivatives. The reaction is suitable for single-step creation of adjacent quaternary stereocenters with high selectivity. We show that, with an appropriate choice of the chiral catalyst and the stereoisomeric prenyl substrate, full control of the stereo- and enantioselectivity is possible in the reaction.