Asymmetric hydroxylative phenol dearomatization through in situ generation of iodanes from chiral iodoarenes and m-CPBA.
'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.
Quideau
Stéphane
S
Université de Bordeaux, Institut des Sciences Moléculaires (CNRS UMR 5255), 2 rue Robert Escarpit, 33607 Pessac Cedex, France. s.quideau@iecb.u-bordeaux.fr
Lyvinec
Gildas
G
Marguerit
Mélanie
M
Bathany
Katell
K
Ozanne-Beaudenon
Aurélie
A
Buffeteau
Thierry
T
Cavagnat
Dominique
D
Chénedé
Alain
A