Remarkably mild and simple preparation of sulfenate anions from beta-sulfinylesters: a new route to enantioenriched sulfoxides.
[reaction: see text] A general, efficient, and experimentally simple method for the generation of sulfenate salts has been developed using beta-sulfinylesters as substrates. The process is based on a retro-Michael reaction, initiated by deprotonation at low temperature. Upon treatment with alkyl halides, the liberated sulfenates are subsequently converted into sulfoxides in good to excellent yield. Extension of the methodology to an unprecedented access to nonracemic sulfoxides by introduction of an enantiopure ligand, (-)-sparteine, is also described.
Caupène
Caroline
C
Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ENSICaen-Université de Caen Basse-Normandie, 6 Boulevard du Maréchal Juin, 14050 Caen, France.
Boudou
Cédric
C
Perrio
Stéphane
S
Metzner
Patrick
P