Asymmetric synthesis catalyzed by chiral ferrocenylphosuphine—metal complexes

Abstract

Optically active ferrocenylphosuphines containing, on the side chain, hydroxy group appropriately distant from the ferrocene nucleus have been found to be effective ligands for the palladium-catalyzed asymmetric allylic alkylation of 1,3-disubstituted 2-propenyl acetates with sodium acetylacetonate and related soft carbon nucleophiles to give the alkylation products of up to 96% ee. A gold(I) complex of the chiral ferrocenylphosuphines which have tertiary amines on the side chain have been found to catalyze the reaction of methyl isocyanoacetate with aldehydes in dichloromethane to give optically active trans-4-methoxycarbonyl-5-alkyl-2-oxazolines with high enantioselectivity (up to 98% ee) in a quantitative yield. © 1988 IUPAC