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The
product distribution of ethers formed from the reaction of
cinnamyl alcohol with orthoesters in the presence of indium (III)
triflate (InOTf)3 is dependent on both the reaction temperature
and catalyst loading. Carrying out the reaction at room temperature
under low loadings of the catalyst leads to a facile reaction generating
the unexpected secondary allyl ether as the major product. In contrast,
carrying out the reaction under higher catalyst loadings at elevated
temperatures provides the expected primary linear ether in high yield
and with excellent selectivity. The etherification reaction is also
effective in the presence of acetals and ketals in place of orthoesters
and allows for the development of the procedure to encompass a telescoped
etherification protocol in which the acetal is generated in situ.
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