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

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 org anic synthesis. These heterocycles, in reacting with a number of carbonyl-r elated compounds (aldehydes, imines, heteroatom-stabilized carbenium ions), act as vinylogous nucleophile modules giving rise to a myriad of functiona lity-rich aldol-type constructs. These, in turn, represent invaluable synth etic platforms onto which a limitless number of functional elements and cho sen chirality may be introduced. Eleven syntheses, amongst the most appeali ng of 1991-1999, have been chosen to illustrate the potentiality of silylox y diene chemistry.