119544-94-4Relevant articles and documents
Iridium-catalyzed enantioselective allyl-allylsilane cross-coupling
Hamilton, James Y.,Hauser, Nicole,Sarlah, David,Carreira, Erick M.
supporting information, p. 10759 - 10762 (2015/05/13)
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. Enantioselective allyl-allylsilane cross-coupling between branched racemic allylic alcohols and allylsilanes was developed. An Ir-(P,olefin) catalyst in conjunction with Sc(OTf)3 as the acidic promoter enables the preparation of chiral 1,5-dienes with up to 99 % ee. The described method was successfully applied to the asymmetric synthesis of the pyrethroid insecticide protrifenbute. cod=1,5-cyclooctadiene, Tf=trifluoromethanesulfonyl.