Synthesis of α-alkoxysilanes: Birch reduction of 2-trialkylsilylfurans

Article abstract of DOI:10.1016/S0040-4039(96)02101-6

The Bitch reduction of (2-trialkylsilyl)furan-3-carboxylic acids has been applied to the synthesis of methyl (2-trialkylsilyl)tetrahydrofuran-3-carboxylates. It is believed that the silicon moiety in such substrates controls the sense of asymmetric induction observed in Michael reactions of the derived enolates with methyl cinnamate. Mild oxidative removal of the silicon moiety generates an oxonium cation which undergoes nucleophilic capture to afford a functionalised furanopyran. Copyright (C) 1996 Elsevier Science Ltd.