RT info:eu-repo/semantics/article
T1 Influence of the substituents on the opening of silylepoxy alcohols: 5-exo-cyclization towards tetrahydrofurans vs. unexpected side reaction leading to tetrahydropyrans
A1 Díez Poza, Carlos
A1 Barbero Pérez, María Asunción
K1 Química orgánica
K1 Organic chemistry
K1 Tetrahydropyrans
K1 Tetrahydrofurans
K1 Cyclization
K1 Epoxysilyl alcohols
K1 Side reaction
K1 Tandem process
AB The regioselective ring opening of epoxy alcohols is an effective method for the synthesis of different types of oxacycles. The 5-exo opening being preferred vs. the 6-endo mode, according to Baldwin rules, the use of silyl-substituted oxiranes has been reported as a possible method to favor the 6-endo cyclization. However, there is a need for a detailed study on the different factors (structural factors, catalyst nature or conditions) that influence this process. In this paper, the acid-catalyzed cyclization of epoxysilyl alcohols was studied, focusing on the effect of substituents and reaction conditions on the outcome of the process. Two types of heterocycles (tetrahydrofurans or tetrahydropyrans) were selectively obtained depending on the structure of the initial epoxysilyl alcohol. Interestingly, cyclization of hindered epoxysilyl alcohols mainly proceeds through an unexpected side reaction, which implies a previous isomerization to an aldehyde. A mechanistic proposal for the formation of the different products is presented.
PB MDPI
SN 1420-3049
YR 2021
FD 2021
LK https://uvadoc.uva.es/handle/10324/59213
UL https://uvadoc.uva.es/handle/10324/59213
LA eng
NO Molecules, 2021, Vol. 26, Nº. 23, 7386
NO Producción Científica
DS UVaDOC
RD 17-jul-2024