Control of γ vs. ε Regioselectivity on the Nucleophilic Addition of 2,4-Pentadienylstannane to Aldehydes by Lewis Acid Co-ordination

Article abstract of DOI:10.1246/cl.1988.225

The BF3-mediated nucleophilic addition of 2- and 4-methoxymethyl-2,4-pentadienylstannanes to aldehydes selectively gives the corresponding γ adducts, while the reaction with sterically hindered aldehydes affors the corresponding ε adducts regardless of the tin reagents applied.