A straightforward enantioselective route to dialkyl sulfoxides based upon two carbon-for-carbon substitution reactions on the sulfinyl group.
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.
Capozzi
Maria Annunziata M
MA
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.
Cardellicchio
Cosimo
C
Naso
Francesco
F
Rosito
Valerio
V