Abstract
Reaction of cyclic sulfites or carbonates of γ,δ-dihydroxy ( E)-α,β-enoates with R 2Cu(CN)Li 2, BF 3; RCu(CN)Li, BF 3(R = Me-, n-Bu-) afforded either diastereoselective S N2′products or reductive elimination product depending on reaction conditions. Addition of R 2Cu(CN)Li 2, BF 3(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, (2 S, 5 S)- trans-2-methyl-5-hexanolide, the pheromone of the carpenter bee Xylocopa hirutissima was synthesized.
Published Version
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