title: A straightforward enantioselective route to dialkyl sulfoxides based upon two carbon-for-carbon substitution reactions on the sulfinyl group.
abstract: Benzyl p-bromophenyl sulfoxide 1 was obtained on a multigram scale and in an enantiomerically pure form by an enantioselective catalytic oxidation, using tert-butyl hydroperoxide in the presence of chiral titanium complexes. Some mechanistic and stereochemical features of interest were studied in this process. Compound 1 was then subjected to two different substitution reactions with Grignard reagents, which caused two sequentially stereocontrolled carbon-for-carbon displacements, leading to chiral nonracemic dialkyl sulfoxides.
authors.affiliation: Consiglio Nazionale delle Ricerche, Istituto di Chimica dei Composti OrganoMetallici, Sezione di Bari and Dipartimento di Chimica, Università di Bari, via Orabona 4, 70126 Bari, Italy.
authors.forename: Maria Annunziata M
authors.initials: MA
authors.lastname: Capozzi
authors.forename: Cosimo
authors.initials: C
authors.lastname: Cardellicchio
authors.forename: Francesco
authors.initials: F
authors.lastname: Naso
authors.forename: Valerio
authors.initials: V
authors.lastname: Rosito