Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes
Journal of the American Chemical Society
A new reactivity in organocatalysis is proposed to account for the coupling of carboxylic acids to α-branched aldehydes by combining primary amine catalysis and an oxidant. The developed methodology is an enantioselective α-coupling of aromatic and aliphatic carboxylic acids to α-branched aldehydes and proceeds in high yields (up to 97%) and for most examples good enantioselectivities (up to 92% ee). On the basis of experimental and mechanistic observations, the role of the primary amine catalyst is discussed.
Leth, L. A., Næsborg, L., Reyes-Rodriguez, G. J., Tobiesen, H. N., Iversen, M. C., & Jørgensen, K. A. (2018). Enantioselective Oxidative Coupling of Carboxylic Acids to α-Branched Aldehydes. Journal of the American Chemical Society, 140, (40), 12687 - 12690. https://doi.org/10.1021/jacs.8b07394. Retrieved from https://nsuworks.nova.edu/cnso_chemphys_facarticles/262