Sequential stereoselective catalysis: Two single-flask reactions of a substrate in the presence of a bifunctional chiral ligand and different transition metals

A new bifunctional ligand capable of promoting different stereoselective catalytic transformations in combination with different transition metals has been prepared by connecting with a spacer a bis(oxazoline) to dihydroquinidine; this ligand was employed in a one-flask procedure in which methyl (E)-3-(4-vinylphenyl)propenoate underwent first cyclopropanation at the electron-rich double bond and then dihydroxylation at the electron-poor alkene to afford a product containing four stereocenters with complete regiocontrol and high stereoselectivity. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).