ol402425u_si_002.cif (30.59 kB)

Multicomponent Prins Cyclization from Allylsilyl Alcohols Leading to Dioxaspirodecanes

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posted on 18.10.2013 by Asunción Barbero, Alberto Diez-Varga, Francisco J. Pulido
A multicomponent reaction for the preparation of dioxaspirodecanes starting from allylsilyl alcohols was achieved. The one-pot sequence involves the sequential acid-catalyzed reaction of an allylsilyl alcohol with an aldehyde to afford an alkenediol. The subsequent Prins cyclization of the homoallylic alcohol moiety generates a tetrahydropyranyl carbocation which is intramolecularly trapped by the second hydroxyl group. The chemoselectivity of the process shows dependence on the nature of the aldehyde and the concentration of the catalyst.