Abstract
A variety of aldehydes undergo a tandem acetalization and intramolecular Prins cyclization with pent-4-ene-1,2-diol in the presence of 5mol% scandium triflate and 15mol% p-toluenesulfonic acid (TsOH) in dichloroethane at 80°C to produce the corresponding bicyclic ethers, that is, 2,6-dioxabicyclo[3,2,1]octane derivatives in good yields and with high selectivity. The salient features of this methodology are higher yields, lower catalyst loadings, and faster reaction times. The combination of Sc(OTf)3 and TsOH (1:3) was found to be more effective than either Sc(OTf)3 or TsOH alone.
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