Organic & Biomolecular Chemistry 2012-11-21

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

Pipas Saha, Priya Ghosh, Sabera Sultana, Anil K Saikia

Index: Org. Biomol. Chem. 10(43) , 8730-8, (2012)

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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.