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Diez De La Varga, Alberto Barbero San Juan, Héctor Pulido Pelaz, Francisco José González Ortega, Alfonso Barbero Pérez, María Asunción 2024-02-14T13:01:10Z 2024-02-14T13:01:10Z 2014 Chem. Eur. J. 2014, 20, 14112 – 14119 0947-6539 https://uvadoc.uva.es/handle/10324/66256 10.1002/chem.201403421 14112 43 14119 Chemistry – A European Journal 20 1521-3765 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. eng info:eu-repo/semantics/restrictedAccess http://creativecommons.org/licenses/by-nc-nd/4.0/ Wiley Attribution-NonCommercial-NoDerivatives 4.0 Internacional Competitive Silyl–Prins Cyclization versus Tandem Sakurai–Prins Cyclization: An Interesting Substitution Effect info:eu-repo/semantics/article