SYNTHESIS OF ALPHA-ALKOXYSILANES - BIRCH REDUCTION OF 2-TRIALKYLSILYLFURANS

The Birch reduction of (2-trialkysilyl)furan-3-carboxylic acids has be en applied to the: synthesis of methyl (2-trialkylsilyl)tetrahydrofura n-3-carboxylates. It is believed that the silicon moiety in such subst rates controls the sense of asymmetric induction observed in Michael r eactions of the derived enolates with methyl cinnamate. Mild oxidative removal of the silicon moiety generates an oxonium cation which under goes nuetrophilic capture to afford a functionalised furanopyran. Copy right (C) 1996 Elsevier Science Ltd