Kinetic resolution of diols and pyridyl alcohols by Cu(II)(borabox)-catalyzed acylation

Clément Mazet; Stephen Roseblade; Valentin Köhler; Andreas Pfaltz

doi:10.1021/ol060443t

Kinetic resolution of diols and pyridyl alcohols by Cu(II)(borabox)-catalyzed acylation

Org Lett. 2006 Apr 27;8(9):1879-82. doi: 10.1021/ol060443t.

Authors

Clément Mazet¹, Stephen Roseblade, Valentin Köhler, Andreas Pfaltz

Affiliation

¹ Department of Chemistry, University of Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.

PMID: 16623574
DOI: 10.1021/ol060443t

Abstract

[reaction: see text] Boron-bridged bisoxazoline (borabox) ligands have been used in the copper(II)-catalyzed benzoylation of pyridyl alcohols and 1,2-diols. Efficient kinetic resolution of 1,2-diols was achieved using both borabox and bisoxazoline (box) ligands. Borabox ligands induced high selectivities in the benzoylation of suitable pyridyl alcohols, where they outperformed bisoxazolines. In addition, highly enantioselective Cu(II)(borabox)-catalyzed benzoylation has been used for the synthesis of both enantiomers of a pyridyl alcohol.