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Diastereoselective IBX Oxidative Dearomatization of Phenols by Remote Induction: Towards the Epicocconone Core Framework
Author(s) -
Boulangé Agathe,
Peixoto Philippe A.,
Franck Xavier
Publication year - 2011
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.201101681
Subject(s) - phenols , chemistry , oxidative phosphorylation , organic chemistry , core (optical fiber) , combinatorial chemistry , computer science , biochemistry , telecommunications
The IBX twist does it : Towards the synthesis of a recently isolated dihydropyranic azaphilone core framework, a 2‐iodoxybenzoic acid (IBX)‐mediated oxidative dearomatization was performed on a bicyclic substrate with excellent diastereoselectivity. Trifluoroacetic acid (TFA) esters were obtained as single diastereomers and water was shown to increase both the speed and diastereoselectivity of the reaction (see scheme).