| Summary: | 32 p. Catalytic, enantioselective halocarboxylation of unsaturated alcohols was developed. Carbonic acid monoalkyl esters were prepared in situ as key intermediates through an equilibrium process under carbon dioxide atmosphere. N-Iodosuccinimide was added as an iodinating reagent and the reaction was kept at a low temperature to optimize enantioselectivity. Bis(AMidine)-based protic acid complexes were used to catalyze the reaction. The reactivity and selectivity were optimized by altering the reaction conditions: both lowered catalyst loading and temperature improved the desired enantiomeric excess (%ee) of the product, but it was achieved at the expense of lower yield; longer reaction time and the use of a solvent mixture, on the other hand, increased the conversion. Purification and characterization of the products were successfully carried out. Chemistry Department. Vanderbilt University. Nashville, Tennessee.
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