RT info:eu-repo/semantics/article
T1 Terminal cyclopropylsilyl alcohols as useful key units to access 2,3,4,6-tetrasubstituted tetrahydropyran scaffolds by stereocontrolled prins cyclization
A1 Fernández Peña, Laura
A1 Barbero Pérez, María Asunción
K1 Química Orgánica
K1 Alcohols
K1 Aldehydes
K1 Aromatic compounds
K1 Cyclization
K1 Hydrocarbons
K1 23 Química
AB In this study, the use of terminal cyclopropylsilyl alcohols in Prins cyclization is reported as a very efficient methodology for the preparation of polysubstituted tetrahydropyrans, in which three new stereogenic centers have been created in a single pot. The reaction is general for a wide variety of aldehydes (alkylic, vinylic, aromatic, or dialdehydes), different types of alcohols, and halogenation agents providing high yields and excellent diastereoselectivity 2,3,4,6-tetrasubstituted tetrahydropyranyl frameworks. Interestingly, diastereomeric alcohols provide the same tetrahydropyranyl derivatives, showing that the reaction mechanism proceeds through common intermediates.
PB ACS (American Chemical Society)
SN 1523-7060
YR 2024
FD 2024
LK https://uvadoc.uva.es/handle/10324/73868
UL https://uvadoc.uva.es/handle/10324/73868
LA eng
NO Organic Letters, 2024, vol. 26, n. 24, p. 5202-5207
NO Producción Científica
DS UVaDOC
RD 22-ene-2025