Stereoselective OsO4-mediated dihydroxylation of β-substituted α-trialkylsilyl-β,γ-unsaturated esters

Abstract

The dihydroxylation of various of α-trialkylsilyl-β,γ-unsaturated esters with OsO4 and NMO has been explored. It has been revealed that these reactions readily allow for a stereoselective dihydroxylation with high levels of dr (>20/1) to afford anti-aldol products with three contiguous stereogenic centers in modest overall yields.

Keywords

• Allylsilane
• Dihydroxylation
• Natural products
• Olefination
• Diastereoselective synthesis