A New Asymmetric Carbon–Carbon Bond Forming Reaction: Four-Component Stereoselective Synthesis of (Z)-4,6-Dihydroxy-3-methylalk-2-enyl Methyl Sulfones

Abstract

The combination of enantiomerically pure 2-methyl-1-alkoxybutadiene with enoxysilanes, SO2, and (following desilylation with Bu4NF) methyl iodide represents a four-component synthesis of (Z)-4,6-hydroxy-3-methylalk-2-enyl methyl sulfones 1 (R=Me, Ph; R′=H). The products are obtained with high stereoselectivity (99.4 % ee).