Addition of Organocopper Reagents to Cyclic Sulfites or Carbonates of γ,δ-Dihydroxy (E)-α,β-Enoates

Article abstract of DOI:10.1016/S0957-4166(00)80506-6

Reaction of cyclic sulfites or carbonates of γ,δ-dihydroxy (E)-α,β-enoates with R2Cu(CN)Li2, BF3; RCu(CN)Li, BF3 (R=Me-, n-Bu-) afforded either diastereoselective S_N2' products or reductive elimination product depending on reaction conditions.Addition of R2Cu(CN)Li2, BF3 (R=Me-, n-Bu-) to cyclic sulfite (1) or cyclic carbonate (3) (inverse addition) afforded highly regio-, (E)-stereo- and diastereoselectivity α-alkylation products (6 and 8).By using this methodology, (2S, 5S)-trans-2-methyl-5-hexanolide, the pheromone of the carpenter bee Xylocopa hirutissima was synthesized.