摘要：

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 SN2′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 diastereoselectively 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.

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