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  • Title: Competitive silyl-Prins cyclization versus tandem Sakurai-Prins cyclization: an interesting substitution effect.
    Author: Diez-Varga A, Barbero H, Pulido FJ, González-Ortega A, Barbero A.
    Journal: Chemistry; 2014 Oct 20; 20(43):14112-9. PubMed ID: 25196494.
    Abstract:
    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 (R(2)≠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.
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