화학공학소재연구정보센터
Journal of the American Chemical Society, Vol.136, No.31, 10886-10889, 2014
Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (+/-)-Pregabalin
The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photo-redox catalysis. Photon-induced oxidation of a broad series of carboxylic acids, including hydrocarbon-substituted, alpha-oxy, and alpha-amino acids, provides a versatile CO2-extrusion platform to generate Michael donors without the requirement for organometallic activation or propagation. A diverse array of Michael acceptors is amenable to this new conjugate addition strategy. An application of this technology to a three-step synthesis of the medicinal agent pregabalin (commercialized by Pfizer under the trade name Lyrica) is also presented.