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

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 (TMSOT...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-11, Vol.10 (43), p.8730-8738
Main Authors: Saha, Pipas, Ghosh, Priya, Sultana, Sabera, Saikia, Anil K
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Catalysis
Cyclization
Epoxy Compounds - chemistry
Esters - chemistry
Mesylates - chemistry
Molecular Structure
Pyrans - chemical synthesis
Pyrans - chemistry
Stereoisomerism
Trimethylsilyl Compounds - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob26088c