Operationally simple, efficient, and diastereoselective synthesis of cis-2,6-disubstituted-4-methylene tetrahydropyrans catalyzed by triflic acid.
[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.
Puglisi
Alessandra
A
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA.
Lee
Ai-Lan
AL
Schrock
Richard R
RR
Hoveyda
Amir H
AH
D002384:Catalysis; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D008698:Mesylates; D011714:Pyrans; C012077:trifluoromethanesulfonic acid