Mild and rapid method for the generation of ortho-(naphtho)-quinone methide intermediates

Shaikh, A. K., Cobb, A. J. A. and Varvounis, G. (2012) Mild and rapid method for the generation of ortho-(naphtho)-quinone methide intermediates. Organic Letters, 14 (2). pp. 584-587. ISSN 1523-7060 doi: 10.1021/ol203196n

Abstract/Summary

A new mild method has been devised for generating o-(naphtho)quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl(or 1-naphthylmethyl) nitrate. The reactive o-(naphtho)quinone methide intermediates were trapped by C, O, N and S nucleophiles and underwent “inverse electron-demand” hetero Diels- Alder reaction with dienophiles to give stable adducts. The method has useful potential application in natural product synthesis and drug research