Intramolecular Diels-Alder reaction of furans with allenyl ethers followed by trimethylsilyl group 1,2-rearrangement and Brook rearrangement

Abstract

The base-catalyzed intramolecular Diels-Alder reactions of 5-trimethylsilyl-2-furfuryl propargyl ethers la-lf gave compounds 2a-2f and 3a-3f in 70-90% yields respectively, a novel reaction involving an intramolecular Diels-Alder reaction followed by a trimethylsilyl group 1,2-rearrangement and Brook rearrangement. Copyright (C) 1996 Elsevier Science Ltd