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- Title
Diastereoselective Synthesis of cis -2,6-Disubstituted Dihydropyrane Derivatives through a Competitive Silyl-Prins Cyclization versus Alternative Reaction Pathways.
- Authors
Peña, Laura F.; López, Enol; Sánchez-González, Ángel; Barbero, Asunción
- Abstract
A convenient regioselective synthesis of allyl- and vinylsilyl alcohols, from a common precursor, was described, by selecting the appropriate reaction conditions. Allyl- and vinylsilyl alcohols were tested in silyl-Prins cyclizations for the preparation of disubstituted oxygenated heterocycles in a one-pot sequential reaction. The methodology was sensitive to the structure of the starting alkenylsilyl alcohol and reaction conditions, with competitive pathways observed (particularly for allylsilyl alcohols), such as Peterson elimination and oxonia-Cope reactions. However, the use of vinylsilyl alcohols allowed the preparation of differently disubstituted cis-2,6-dihydropyrans in moderate to good yields. Computational studies support the proposed mechanism.
- Subjects
RING formation (Chemistry); ELIMINATION reactions; SILYL ethers; ALCOHOL; HETEROCYCLIC compounds
- Publication
Molecules, 2023, Vol 28, Issue 7, p3080
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28073080