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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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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	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.
doi_str_mv	10.1016/j.tetlet.2011.03.024
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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
title	New very mild conditions for the opening of an epoxide assisted by a neighboring carbonyl group
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