Abstract
The application of hydroformylation to substrates containing hydroxyl groups tends to be problematic because the formed aldehydes can react with the hydroxyl moiety in undesired ways. Herein we describe a protocol in which the hydroxyl group is O-acylated concomitantly with hydroformylation in a one-pot catalytic process, preventing undesired side reactions. This strategy is applied for the renewable terpenes perillyl alcohol, carveol, myrtenol, and isopulegol, as well as for isoprenol and the biomass-based nopol. The selectivity for the acetoxyaldehydes is much higher than for the analogous hydroxyaldehydes produced by hydroformylation only. Furthermore, the new products obtained through a synthetically efficient process directly from renewable resources are promising candidates to new fragrance components as they contain aldehyde and acetoxy ester functionalities, both known to aggregate olfactory properties to molecules.
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