Palladium-catalyzed gamma-selective and stereospecific allyl-aryl coupling between allylic acetates and arylboronic acids.

ABSTRACT

Allyl-aryl coupling between allylic acetates and arylboronic acids took place in the presence of catalytic amounts of Pd(OAc)(2), 1,10-phenanthroline, and AgSbF(6) with high gamma-selectivity and E/Z-selectivity. The reaction of an optically active allylic acetates with an alpha-stereogenic center proceeded with excellent alpha-to-gamma chirality transfer with syn-selectivity and gave the corresponding optically active allyl-aryl coupling products with a stereogenic center at the benzylic position.