Next Article in Journal
Esterified Soy Proteins with Enhanced Antibacterial Properties for the Stabilization of Nano-Emulsions under Acidic Conditions
Next Article in Special Issue
Synthesis and Properties of 1,3-Disubstituted Ureas Containing (Adamantan-1-yl)(phenyl)methyl Fragment Based on One-Pot Direct Adamantane Moiety Inclusion
Previous Article in Journal
Effect of Wheat-Derived Arabinoxylan on the Gut Microbiota Composition and Colonic Regulatory T Cells
Previous Article in Special Issue
Ugi Four-Component Reactions Using Alternative Reactants
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 28
Issue 7
10.3390/molecules28073080
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

Diastereoselective Synthesis of cis-2,6-Disubstituted Dihydropyrane Derivatives through a Competitive Silyl-Prins Cyclization versus Alternative Reaction Pathways

by
Laura F. Peña
1,
Enol López
1,
Ángel Sánchez-González
1,2 and
Asunción Barbero
1,*
1
Department of Organic Chemistry, Campus Miguel Delibes, University of Valladolid, 47011 Valladolid, Spain
2
BioISI-Biosystems and Integrative Sciences Institute, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal
*
Author to whom correspondence should be addressed.
Molecules 2023, 28(7), 3080; https://doi.org/10.3390/molecules28073080
Submission received: 20 February 2023 / Revised: 20 March 2023 / Accepted: 27 March 2023 / Published: 30 March 2023
(This article belongs to the Special Issue Green and Highly Efficient One-Pot Synthesis and Catalysis)
Browse Figures
Versions Notes

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.
Keywords: Prins cyclization; heterocycles; oxacycles Prins cyclization; heterocycles; oxacycles

Share and Cite

MDPI and ACS Style

Peña, L.F.; López, E.; Sánchez-González, Á.; Barbero, A. Diastereoselective Synthesis of cis-2,6-Disubstituted Dihydropyrane Derivatives through a Competitive Silyl-Prins Cyclization versus Alternative Reaction Pathways. Molecules 2023, 28, 3080. https://doi.org/10.3390/molecules28073080

AMA Style

Peña LF, López E, Sánchez-González Á, Barbero A. Diastereoselective Synthesis of cis-2,6-Disubstituted Dihydropyrane Derivatives through a Competitive Silyl-Prins Cyclization versus Alternative Reaction Pathways. Molecules. 2023; 28(7):3080. https://doi.org/10.3390/molecules28073080

Chicago/Turabian Style

Peña, Laura F., Enol López, Ángel Sánchez-González, and Asunción Barbero. 2023. "Diastereoselective Synthesis of cis-2,6-Disubstituted Dihydropyrane Derivatives through a Competitive Silyl-Prins Cyclization versus Alternative Reaction Pathways" Molecules 28, no. 7: 3080. https://doi.org/10.3390/molecules28073080

APA Style

Peña, L. F., López, E., Sánchez-González, Á., & Barbero, A. (2023). Diastereoselective Synthesis of cis-2,6-Disubstituted Dihydropyrane Derivatives through a Competitive Silyl-Prins Cyclization versus Alternative Reaction Pathways. Molecules, 28(7), 3080. https://doi.org/10.3390/molecules28073080

Article Metrics

Back to TopTop