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Oxidation of α‐Alkoxy Allenes into α′‐Alkoxy Enones
Author(s) -
Cordier Pierre,
Aubert Corinne,
Malacria Max,
Gandon Vincent,
Lacôte Emmanuel
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000914
Subject(s) - alkoxy group , allene , regioselectivity , chemistry , oxidative phosphorylation , medicinal chemistry , organic chemistry , catalysis , biochemistry , alkyl
Rearrangement enablers : α‐Alkoxy allenes undergo regioselective oxidative migration to give α′‐alkoxy enones in good to excellent yields (see scheme; Bn=benzyl, m CPBA= m ‐chloroperbenzoic acid). The influence of substituents on the allene, at C1, and at the oxygen atom has been examined. In addition, an oxidative cascade delivers α′‐alkoxy oxiranyl ketones through diepoxidation.