RT info:eu-repo/semantics/article
T1 Competitive Silyl–Prins Cyclization versus Tandem Sakurai–Prins Cyclization: An Interesting Substitution Effect
A1 Diez de la Varga, Alberto
A1 Barbero San Juan, Héctor
A1 Pulido Pelaz, Francisco José
A1 González Ortega, Alfonso
A1 Barbero Pérez, María Asunción
AB Two different mechanism pathways are observed for the reaction of allylsilyl alcohols 1 and aldehydes in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf). In the case of allylsilyl alcohols without allylic substituents, the reaction gives dioxaspirodecanes, which are the products of a tandem Sakurai–Prins cyclization. In contrast, allylsilyl alcohols with an allylic substituent (R2¼6 H) selectively provide oxepanes, thus corresponding to a direct silyl–Prins cyclization. Both types of product are obtained with excellent stereoselectivity. Theoretical studies have been performed to obtain some rationalization for the observed stereoselectivity.
PB Wiley
SN 0947-6539
YR 2014
FD 2014
LK https://uvadoc.uva.es/handle/10324/66256
UL https://uvadoc.uva.es/handle/10324/66256
LA eng
NO Chem. Eur. J. 2014, 20, 14112 – 14119
NO Producción Científica
DS UVaDOC
RD 07-ago-2024