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Journal of the American Chemical Society

A dramatic switch of enantioselectivity in asymmetric heck reaction by benzylic substituents of ligands.


PMID 18590334

Abstract

A series of benzylic substituted P, N-ligands 1 and 2 have been synthesized. The Pd-complexes of these ligands show high catalytic activity and enantioselectivity in catalyzing the asymmetric Heck reaction. A dramatic switch in enantioselectivity is realized using ligands with and without substituents at the benzylic position of the ligand. Ligands 1 with H as the substituents offer products in (R)-configuration while ligands 2 with the methyl as substituents result in (S)-configuration products. In most cases high enantioselectivities are achieved. Density functional theory calculations on the reaction mechanism as well as X-ray analysis of 1a-PdCl 2 and 2a-PdCl 2 complexes provide a rational explanation for the above observations.

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