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Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India
E-mail: asaikia@iitg.ernet.in
; Fax: +91 361 269 0762
; Tel: +91 361 258 2316
Org. Biomol. Chem., 2012,10, 8730-8738
DOI:
10.1039/C2OB26088C
Received
06 Jun 2012,
Accepted
12 Sep 2012
First published online
12 Sep 2012
Substituted dihydropyrans can be efficiently synthesized in good yields with excellent diastereoselectivity from the reaction of aldehydes or epoxides and ethyl 3-alkyl-3-hydroxy-5-methylhex-5-enoate via an oxonium–ene cyclization reaction catalyzed by trimethylsilyl trifluoromethanesulfonate (TMSOTf) under mild conditions.