RT info:eu-repo/semantics/article
T1 Diastereoselective synthesis of cis-2,6-disubstituted dihydropyrane derivatives through a competitive silyl-prins cyclization versus alternative reaction pathways
A1 Fernández Peña, Laura
A1 López Hernández, Enol
A1 Sánchez González, Ángel
A1 Barbero Pérez, María Asunción
K1 Heterocyclic compounds
K1 Compuestos heterocíclicos
K1 Analytical chemistry
K1 Prins cyclization
K1 Oxacycles
K1 2301 Química Analítica
AB 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.
PB MDPI
SN 1420-3049
YR 2023
FD 2023
LK https://uvadoc.uva.es/handle/10324/63811
UL https://uvadoc.uva.es/handle/10324/63811
LA eng
NO Molecules, 2023, Vol. 28, Nº. 7, 3080
NO Producción Científica
DS UVaDOC
RD 12-may-2024