Stereoselective synthesis of 2,3-epoxy alcohols mediated by a remote sulfinyl group

The influence of the sulfinyl group as a chiral auxiliary in the stereoselective addition of oxiranyllithiums to ( S)-2- p-tolylsulfinylbenzaldehyde has been studied. All reactions evolve with retention of configuration at the starting lithiated carbon. Completely stereoselective additions have been...

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Bibliographic Details
Published in:Tetrahedron 2010-02, Vol.66 (8), p.1581-1585
Main Authors: García Ruano, José Luis, Martín-Castro, Ana M., Tato, Francisco, Torrente, Esther, Tocco, M. Giovanna, Florio, Saverio, Capriati, Vito
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:The influence of the sulfinyl group as a chiral auxiliary in the stereoselective addition of oxiranyllithiums to ( S)-2- p-tolylsulfinylbenzaldehyde has been studied. All reactions evolve with retention of configuration at the starting lithiated carbon. Completely stereoselective additions have been observed when configurations at sulfur and the lithiated carbon are different (matched pair), whereas variable dr's values (ranging between 52:48 and >99:
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.12.006