Reformatsky-type reaction of chiral nonracemic alpha-bromo-alpha'-sulfinyl ketones with aldehydes. Synthesis of enantiomerically pure 2-methyl-1,3-diol moieties.
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.
Obringer
Michel
M
Laboratoire de Stéréochimie Associé au CNRS, Université Louis Pasteur, E.C.P.M, 25 rue Becquerel, 67087 Strasbourg Cedex 2, France.
Colobert
Françoise
F
Neugnot
Benjamin
B
Solladié
Guy
G