New very mild conditions for the opening of an epoxide assisted by a neighboring carbonyl group

An epoxide is opened stereo- and regio-selectively by 1,3-endo migration of a phenylthiogroup in almost neutral conditions. The thioether is then reduced to give the alcohol corresponding to the starting epoxide in an excellent yield.

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Bibliographic Details
Published in:Tetrahedron letters 2011-05, Vol.52 (20), p.2550-2553
Main Authors: Walther, Alexandre, Josien-Lefebvre, Delphine, Le Drian, Claude
Format: Article
Language:English
Subjects:
Alcohols
Carbonyl groups
Chemistry
Epoxide opening
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Intramolecular migration
Iodine catalysis
Migration
Organic chemistry
Preparations and properties
Regioselectivity
Tetrahedrons
Zinc iodide
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Description
Summary:An epoxide is opened stereo- and regio-selectively by 1,3-endo migration of a phenylthiogroup in almost neutral conditions. The thioether is then reduced to give the alcohol corresponding to the starting epoxide in an excellent yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.03.024