The Vinylogous Aldol Addition of Heterocyclic Silyloxy Dienes: Application in Synthesis

Open-chain dienolate motifs, deriving from deprotonation of α,β-unsaturated carbonyl compounds, have been recently introduced as practically applicable building blocks for selective organic synthesis, being used for efficient carbon-carbon bond formation with a number of electrophilic carbonyl-related synthons. Of particular use is that furan-, pyrrole-, and thiophene-derived 2-silyloxy dienes, our research group has been exploiting for about a decade, undergo regio- and stereoselective vinylogous cross-aldol or Mannich-type reactions with production of a wide assortment of functionality dense constructs, when reacted with suitable carbonyl or imino acceptors. This account surveys salient achievements our laboratory realized in the synthesis of biofunctional molecules by treading the quite inexhaustible track of the heterocyclic silyloxy diene chemistry.

silyloxy dienes - vinylogous aldol addition - diastereoselective synthesis - heterocyclic compounds