Sulfoxide‐Directed Stereocontrolled Access to 2 H ‐Chromans: Total Synthesis of the ( S , R , R , R )‐Enantiomer of the Antihypertensive Drug Nebivolol | Zendy

Carreño M. Carmen | Zendy; HernándezTorres Gloria | Zendy; Urbano Antonio | Zendy; Colobert Françoise | Zendy

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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)

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