Collect. Czech. Chem. Commun. 2011, 76, 919-927
https://doi.org/10.1135/cccc2011029
Published online 2011-06-30 13:26:32

Chemoenzymatic dynamic kinetic resolution as a key step in the enantioselective synthesis of (S)-salbutamol

Annika Träffa, Carmen E. Solarteb and Jan-E. Bäckvalla,*

a Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden
b Deparment of Chemistry, Lleida University, 25198 Lleida, Spain

Abstract

The synthesis of (S)-salbutamol is described. By utilizing DKR in the enantiodetermining step, employing Burkholderia cepacia lipase (PS-IM), (S)-acetate ((S)-6) was obtained in excellent enantiomeric excess (98%). The subsequent transformations yielded the salt of (S)-salbutamol with retained stereochemistry.

Keywords: Dynamic kinetic resolution; Kinetic resolution; Enzymatic catalysis; Racemization; Asymmetric synthesis.

References: 28 live references.

This article is part of virtual issue Prof. Pavel Kočovský, FRSE
60th Birthday.