An enantioselective allyl-allylsilane cross-coupling involving racemic branched allylic alcohols and allylsilanes is reported. An iridium-(P,olefin) phosphoramidite complex enables the transformation with high regio- and stereoselectivity under operationally simple conditions. The utility of the coupling is demonstrated in a concise catalytic, enantioselective synthesis of a pyrethroid insecticide protrifenbute.
Keywords: 1,5-diene; allylic substitution; allylsilane; enantioselectivity; iridium.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.