Reformatsky-Type Reaction of Chiral Nonracemic α-Bromo-α‘-sulfinyl Ketones with Aldehydes. Synthesis of Enantiomerically Pure 2-Methyl-1,3-diol Moieties

Chiral nonracemic α-bromo-α‘-sulfinyl ketones were shown to react with aldehydes in the presence of SmI2 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 moi...

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Bibliographic Details
Published in:Organic letters 2003-03, Vol.5 (5), p.629-632
Main Authors: Obringer, Michel, Colobert, Françoise, Neugnot, Benjamin, Solladié, Guy
Format: Article
Language:English
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Summary:Chiral nonracemic α-bromo-α‘-sulfinyl ketones were shown to react with aldehydes in the presence of SmI2 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027223+