The synthetic utility of furan-, pyrrole- and thiophene-based 2-silyloxy dienes

Abstract

The aim of this review is to highlight the utility of a remarkable triad of 2-silyloxy diene synthons derived from furan, pyrrole and thiophene in organic synthesis. These heterocycles, in reacting with a number of carbonyl-related compounds (aldehydes, imines, heteroatom-stabilized carbenium ions), act as vinylogous nucleophile modules giving rise to a myriad of functionality-rich aldol-type constructs. These, in turn, represent invaluable synthetic platforms onto which a limitless number of functional elements and chosen chirality may be introduced. Eleven syntheses, amongst the most appealing of 1991–1999, have been chosen to illustrate the potentiality of silyloxy diene chemistry.