title: Stereoselective synthesis of 2,4,5-trisubstituted tetrahydropyrans using an intramolecular allylation strategy.
abstract: A highly stereoselective route to 2,4,5-trisubstituted tetrahydropyrans is reported. The key step employs an intramolecular allylation of a (Z)-allylsilane onto an aldehyde under Brønsted acid activation. Complete 1,4-stereoinduction accounts for the formation of only two out of the possible four THP products. The level of 1,3-stereoinduction is optimal when the reaction is carried out in an apolar solvent, which is in accord with electrostatics being key to controlling this aspect of the stereoselectivity.
authors.affiliation: School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK.
authors.forename: Peter J
authors.initials: PJ
authors.lastname: Jervis
authors.forename: Benson M
authors.initials: BM
authors.lastname: Kariuki
authors.forename: Liam R
authors.initials: LR
authors.lastname: Cox
mesh_terms: D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011714:Pyrans