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  • Diastereoselective synthesis of substituted dihydropyrans via an oxonium-ene cyclization reaction.

Diastereoselective synthesis of substituted dihydropyrans via an oxonium-ene cyclization reaction.

Organic & biomolecular chemistry (2012-10-06)
Pipas Saha, Priya Ghosh, Sabera Sultana, Anil K Saikia
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Trimethylsilyl trifluoromethanesulfonate, purum, ≥98.0% (T)
Sigma-Aldrich
Trimethylsilyl trifluoromethanesulfonate, 99%