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The Catalyzed Desulfinylative Allylation of Carbonyl Compounds with Alk‐2‐enesulfonyl Chlorides and Silyl Alk‐2‐enesulfinates
Author(s) -
Volla Chandra M. R.,
Marković Dean,
Laclef Sylvain,
Vogel Pierre
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000705
Subject(s) - silylation , sulfonyl , chemistry , nucleophile , catalysis , sulfinic acid , organic chemistry , medicinal chemistry , alkyl
Coupling up with sulfonyl chlorides : An ene reaction of alkenes with SO 2 ⋅BCl 3 permits the one‐pot conversion of simple alkenes into β,γ‐unsaturated sulfonyl chlorides or sulfinic silyl esters. These compounds can then be used as nucleophilic allylating agents with aldehydes and ketones to generate the corresponding homoallylic alcohols (see scheme) with good chemo‐ and diastereoselectivity in the presence of a suitable catalyst and reducing agent.