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Competitive Silyl–Prins Cyclization versus Tandem Sakurai–Prins Cyclization: An Interesting Substitution Effect Diez De La Varga, Alberto Barbero San Juan, Héctor Pulido Pelaz, Francisco José González Ortega, Alfonso Barbero Pérez, María Asunción Producción Científica 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. 2024-02-14T13:01:10Z 2024-02-14T13:01:10Z 2014 info:eu-repo/semantics/article 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 eng https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201403421 info:eu-repo/semantics/restrictedAccess http://creativecommons.org/licenses/by-nc-nd/4.0/ Wiley Attribution-NonCommercial-NoDerivatives 4.0 Internacional Wiley SI