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Highly Diastereoselective Synthesis of Orthoquinone Monoketals through λ 3 ‐Iodane‐Mediated Oxidative Dearomatization of Phenols
Author(s) -
Pouységu Laurent,
Chassaing Stefan,
Dejugnac Delphine,
Lamidey AnneMarie,
Miqueu Karinne,
Sotiropoulos JeanMarc,
Quideau Stéphane
Publication year - 2008
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.200705816
Subject(s) - chemistry , phenols , ring (chemistry) , ligand (biochemistry) , stereochemistry , phenol , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , receptor
Versatile chiral substrates for asymmetric synthesis are formed through the spiroketalization of phenols with a chiral substituted ethanol unit O‐tethered to the ortho position upon treatment with PhI(OAc) 2 (see example; TFE=2,2,2‐trifluoroethanol). Intermediates with a six‐membered iodine(III)‐containing ring (the natural localized molecular orbitals associated with the IC6 bond are shown) undergo ligand coupling to give the spiroketals.