Highly Diastereoselective Synthesis of Orthoquinone Monoketals through λ ³ ‐Iodane‐Mediated Oxidative Dearomatization of Phenols

Abstract

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 IC6 bond are shown) undergo ligand coupling to give the spiroketals. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z705816_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.