CHEMOENZYMATIC ROUTE TO BETA-BLOCKERS VIA 3-HYDROXY ESTERS

Authors
WUNSCHE K SCHWANEBERG U BORNSCHEUER UT MEYER HH
Citation
K. Wunsche et al., CHEMOENZYMATIC ROUTE TO BETA-BLOCKERS VIA 3-HYDROXY ESTERS, Tetrahedron : asymmetry, 7(7), 1996, pp. 2017-2022
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
7
Year of publication
1996
Pages
2017 - 2022
Database
ISI
SICI code
0957-4166(1996)7:7<2017:CRTBV3>2.0.ZU;2-X
Abstract
Enantiomerically pure precursors of beta-blockers (propranolol, alpren olol and 1-(isopropylamino)-3-p-methoxy-phenoxy-2-propanol) were synth esized. Key step is the lipase-catalyzed kinetic resolution of rac-3-h ydroxy esters either by O-acylation using vinyl acetate or by hydrolys is of the eater group. Both approaches were highly enantioselective (> 95%ee) with E-values > 150 using lipase from Pseudomonas cepacia. The formal synthesis of (-)-(S)-propranolol was developed in subsequent s teps. Copyright (C) 1996 Elsevier Science Ltd