title: Reformatsky-type reaction of chiral nonracemic alpha-bromo-alpha'-sulfinyl ketones with aldehydes. Synthesis of enantiomerically pure 2-methyl-1,3-diol moieties.
abstract: Chiral nonracemic alpha-bromo-alpha'-sulfinyl ketones were shown to react with aldehydes in the presence of SmI(2) in a Reformatsky-type reaction to give the corresponding adduct with excellent syn diastereoselectivity. Further reduction of the Reformatsky adducts furnished anti- and syn-2-methyl-1,3-diol moieties in excellent yields and diastereoselectivities.
authors.affiliation: Laboratoire de Stéréochimie Associé au CNRS, Université Louis Pasteur, E.C.P.M, 25 rue Becquerel, 67087 Strasbourg Cedex 2, France.
authors.forename: Michel
authors.initials: M
authors.lastname: Obringer
authors.forename: Françoise
authors.initials: F
authors.lastname: Colobert
authors.forename: Benjamin
authors.initials: B
authors.lastname: Neugnot
authors.forename: Guy
authors.initials: G
authors.lastname: Solladié