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Enzyme‐Mediated Synthesis of ( S )‐ and ( R )‐Verapamil
Author(s) -
Brenna Elisabetta,
Fuganti Claudio,
Grasselli Piero,
Serra Stefano
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200104)2001:7<1349::aid-ejoc1349>3.0.co;2-9
Subject(s) - chemistry , enantioselective synthesis , lipase , verapamil , enantiomer , stereochemistry , acetylation , derivative (finance) , enzyme , allylic rearrangement , alcohol , stereoselectivity , organic chemistry , catalysis , biochemistry , financial economics , economics , gene , calcium
A lipase‐mediated synthesis of ( S )‐ and ( R )‐verapamil is described. The key steps of the synthetic sequence are the enantioselective acetylation, mediated by Lipase PS, of allylic alcohol ( Z )‐(±)‐ 2 , affording the acetate derivative ( Z,R )‐(−)‐ 3 ( ee 92%) and the Ireland−Claisen rearrangement of this latter and of its enantiomer ( Z,S )‐(+)‐ 3 ( ee 92%) to afford acid derivatives ( E,R )‐(−)‐ 4 ( ee 94%) and ( E,S )‐(+)‐ 4 ( ee 93%), precursors of ( S )‐ and ( R )‐verapamil, respectively.