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Asymmetric Hydroxylative Phenol Dearomatization through In Situ Generation of Iodanes from Chiral Iodoarenes and m ‐CPBA
Author(s) -
Quideau Stéphane,
Lyvinec Gildas,
Marguerit Mélanie,
Bathany Katell,
OzanneBeaude Aurélie,
Buffeteau Thierry,
Cavagnat Dominique,
Chénedé Alain
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200901039
′I′ is all the hype : A twofold excess of iodoarene in the title reaction leads to ortho ‐quinols in good yields, whereas organocatalytic versions of this reaction enable subsequent epoxidation in a regio‐ and diastereoselective fashion. Chiral iodobiarenes led to enantioselectivities up to 50 % ee. m ‐CPBA= meta ‐chloroperoxybenzoic acid.