title: Stereoselective synthesis of allylic sulfones via the oxonia-Cope rearrangement of homoallylic alcohols containing a homoallylic sulfone moiety.
abstract: The homoallylic alcohols 3 that can be prepared by the indium-mediated addition of haloallylic sulfones 1 to aldehydes 2 undergo the oxonia-Cope rearrangement with aldehydes 2 to give rise to the allylic sulfones 4 containing a conjugated diene moiety in a highly stereoselective manner. Electron-rich aldehydes preferentially participate in this oxonia-Cope rearrangement with the homoallylic alcohols 3. Excellent correlations of the stereochemistry (anti-3 to trans-allylic sulfone 4 and syn-3 to cis-allylic sulfone 4) have been observed in the oxonia-Cope rearrangement.
authors.affiliation: Department of Chemistry, Department of Nano Science and Engineering, Myong Ji University, Yongin, Kyunggi-Do, 449-728, South Korea.
authors.forename: Se-Young
authors.initials: SY
authors.lastname: Jung
authors.forename: Jae-Hong
authors.initials: JH
authors.lastname: Min
authors.forename: Jung Taek
authors.initials: JT
authors.lastname: Oh
authors.forename: Sangho
authors.initials: S
authors.lastname: Koo