Novel approach to the synthesis of enantioenriched sulfoxides. Highly diastereoselective alkylation of sulfenate anions with 1,4-asymmetric induction.
[reaction: see text] Efficient 1,4-asymmetric induction with an enantiopure aminoalkyl group as the chiral auxiliary has been achieved in the first example of diastereoselective alkylation (up to 98:2) of a sulfenate anion, readily prepared by oxidation of the corresponding thiolate. The stereochemistry of the sulfoxide produced is the opposite of that obtained by the conventional route based on oxidation of the sulfide precursor.
Sandrinelli
Franck
F
Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ISMRA-Université de Caen, 6 Boulevard du Maréchal Juin, F-14050 Caen, France.
Perrio
Stéphane
S
Averbuch-Pouchot
Marie-Thérèse
MT