Asymmetric hydroxylative phenol dearomatization through in situ generation of iodanes from chiral iodoarenes and m-CPBA

Angew Chem Int Ed Engl. 2009;48(25):4605-9. 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.