Electrophile-induced ether transfer: Stereoselective synthesis of 2,6-disubstituted-3,4-dihydropyrans
(Chemical Equation Presented) Stereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans has been achieved from a simple homoallylic alkoxyether via a three-step sequence: electrophile-induced ether transfer, cyclization, and functionalization, which is highlighted by a rare example of Ferrier rearrangement of allylic ether. This methodology was successfully implemented for the asymmetric synthesis of a C7-C17 fragment of swinholide A. © 2008 American Chemical Society.
Publication Source (Journal or Book title)
Journal of Organic Chemistry
Kartika, R., Frein, J., & Taylor, R. (2008). Electrophile-induced ether transfer: Stereoselective synthesis of 2,6-disubstituted-3,4-dihydropyrans. Journal of Organic Chemistry, 73 (14), 5592-5594. https://doi.org/10.1021/jo800704d