Ligand-assisted rate acceleration in transacylation by a yttrium-salen complex. Demonstration of a conceptually new strategy for metal-catalyzed kinetic resolution of alcohols

Mei-Huey Lin; T V RajanBabu

doi:10.1021/ol025809q

Ligand-assisted rate acceleration in transacylation by a yttrium-salen complex. Demonstration of a conceptually new strategy for metal-catalyzed kinetic resolution of alcohols

Org Lett. 2002 May 2;4(9):1607-10. doi: 10.1021/ol025809q.

Authors

Mei-Huey Lin¹, T V RajanBabu

Affiliation

¹ Department of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA.

PMID: 11975640
DOI: 10.1021/ol025809q

Abstract

[reaction: see text]. Yttrium-salen complexes effect transacylation between enolesters and chiral secondary alcohols, resulting in varying degrees of kinetic resolution. Even though the enantioselectivity remains modest (k(fast)/k(slow) up to 4.81), these results represent the first demonstration of a conceptually new metal-catalyzed acyl transfer process that results in kinetic resolution. On the basis of the solid-state structure of the catalyst, a novel associative mechanistic pathway is proposed for the reaction.