Kinetic Resolution of Pyridyl Alcohols by Cu(II)(Borabox)-Catalyzed Acylation

Stephen J. Roseblade; Andreas Pfaltz

doi:10.1055/s-2007-983850

PSP

Kinetic Resolution of Pyridyl Alcohols by Cu(II)(Borabox)-Catalyzed Acylation

Stephen J. Roseblade, Andreas Pfaltz*
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
Fax: +41(61)2671103; e-Mail: andreas.pfaltz@unibas.ch;

Abstract

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Abstract

Kinetic resolution of pyridyl alcohols has been achieved using copper(II)(borabox)-catalyzed benzoylation. Selectivity factors (k_rel) of up to 125 have been observed and application to the synthesis of chiral pyridyl phosphine ligands is described.

Key words

kinetic resolution - asymmetric catalysis - copper - bisoxazoline ligands - pyridines

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Referenzen

References

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Benzoyl chloride has been identified as the optimal acylating reagent for kinetic resolution of 1,2-diols. See reference 6b.

Conversions and enantioselectivities were determined using ee values obtained from chiral HPLC of the products(pr) and starting materials(sm); conversion (C) = ee_sm/(ee_sm + ee_pr). S = ln[1-C(1 + ee_pr)]/ln[1 - C(1 - ee_pr)] = ln[(1 - C)(1 - ee_sm)]/ln[(1 - C)(1 + ee_sm)], see:

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