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Reduction of Alkynyl α‐Hydroxy Esters: Stereoselective α‐Ketol Rearrangement
Author(s) -
Hameury Thomas,
Bellosta Véronique,
Guillemont Jérôme,
Van Hijfte Luc,
Cossy Janine
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901202
Subject(s) - chemistry , stereoselectivity , rearrangement reaction , stereochemistry , cope rearrangement , carroll rearrangement , reaction mechanism , medicinal chemistry , sigmatropic reaction , catalysis , organic chemistry
The α‐ketol rearrangement of tertiary α‐hydroxy esters induced by LiAlH 4 /acid treatment provides α‐hydroxy ketones in good yields and high diastereoselectivity. A mechanism is proposed for this reaction as well as a model to explain the diastereoselectivity of the rearrangement.