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Sulfoxide‐Directed Stereocontrolled Access to 2 H ‐Chromans: Total Synthesis of the ( S , R , R , R )‐Enantiomer of the Antihypertensive Drug Nebivolol
Author(s) -
Carreño M. Carmen,
HernándezTorres Gloria,
Urbano Antonio,
Colobert Françoise
Publication year - 2008
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/ejoc.200800201
Subject(s) - chemistry , enantiomer , stereoselectivity , deoxygenation , sulfoxide , enantioselective synthesis , stereochemistry , lignan , organic chemistry , catalysis
A homochiral sulfoxide‐directed reductive deoxygenation of 2‐( p ‐tolylsulfinyl)methyl‐2‐chromanols allows the stereoselective formation of 2 H ‐chromans with up to 95:5 diastereoisomeric ratio. This new methodology was appliedin a short and convergent enantioselective synthesis ofthe ( S , R , R , R )‐enantiomer of the antihypertensive drugNebivolol.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)