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

Research output: Contribution to journalArticle

65 Citations (Scopus)

Abstract

(matrix presented) Yttrium-salen complexes effect transacylation between enolesters and chiral secondary alcohols, resulting in varying degrees of kinetic resolution. Even though the enantioselectivity remains modest (kfast/kslow 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.

Original languageEnglish
Pages (from-to)1607-1610
Number of pages4
JournalOrganic Letters
Volume4
Issue number9
DOIs
Publication statusPublished - 2002 May 2

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this