Magnesium-mediated intramolecular reductive coupling: a stereoselective synthesis of C2-symmetric 3,4-bis-silyl-substituted adipic acid derivatives

Abstract

Chiral C₂-symmetric 3,4-bis-silyl-substituted adipic acid derivatives have been synthesised by a Mg/trimethylsilyl chloride-mediated intramolecular reductive coupling of symmetrical disiloxanes of β-silylacrylic acid N-oxazolidinone derivatives. Efficient and short syntheses of enantiomerically pure enantiomers of 2,6-dioxabicyclo[3.3.0]octane-3,7-dione have been achieved from the bis-silylated adipic acid derivatives using Fleming–Tamao oxidation as the key step.