title: Operationally simple, efficient, and diastereoselective synthesis of cis-2,6-disubstituted-4-methylene tetrahydropyrans catalyzed by triflic acid.
abstract: [reaction: see text] A highly efficient (0.01 mol % of TfOH), operationally simple (room temperature, inexpensive, and commercially available catalyst), and diastereoselective (up to >98% de) method for Brønsted acid-catalyzed reaction of enol ethers to form cis-2,6-disubstituted tetrahydropyrans is disclosed.
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Puglisi
authors.forename: Ai-Lan
authors.initials: AL
authors.lastname: Lee
authors.forename: Richard R
authors.initials: RR
authors.lastname: Schrock
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
mesh_terms: D002384:Catalysis; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D008698:Mesylates; D011714:Pyrans; C012077:trifluoromethanesulfonic acid