Exploitation of cyclopropane carbaldehydes to prins cyclization: quick access to (E)‑Hexahydrooxonine and Octahydrocyclopenta[b]pyran

Abstract

A single-step TiX4-mediated Prins-type cyclization of cyclopropane carbaldehydes with 3-buten-1-ol for the highly stereoselective construction of relatively strained (E)- hexahydrooxonines is reported. Switching the alcohol to 3- butyn-1-ol prompted a similar route, augmented by another cyclization within a nine-membered ring to afford a bicyclized product (4,4-dihalo-5-aryloctahydrocyclopenta[b]pyran). Easy transformation of the resulting geminal dihalide to a vinyl halide and a ketone further supplemented the substance of this approach.