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Enantioselective Routes to Sulfoxides Based Upon the Use of Carbanionic Leaving Groups
Author(s) -
Capozzi Maria Annunziata M.,
Cardellicchio Cosimo,
Naso Francesco
Publication year - 2004
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.200300497
Subject(s) - chemistry , enantioselective synthesis , stereoselectivity , reagent , sulfide , combinatorial chemistry , sulfoxide , leaving group , stereochemistry , organic chemistry , catalysis
Several carbanionic leaving groups can be easily displaced from the sulfinyl group by organometallic reagents. The reaction follows a highly stereoselective course of inversion of configuration. Provided that a ready route to the precursor sulfinyl compound is available (e.g. an enantioselective oxidation of the corresponding sulfide), the process can be transformed into an easy and versatile procedure for the stereoselective synthesis of sulfoxides. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)