TY - JOUR
T1 - Carboxylic acids as A traceless activation group for conjugate additions
T2 - A three-step synthesis of (±)-pregabalin
AU - Chu, Lingling
AU - Ohta, Chisa
AU - Zuo, Zhiwei
AU - MacMillan, David W.C.
PY - 2014/8/6
Y1 - 2014/8/6
N2 - The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced oxidation of a broad series of carboxylic acids, including hydrocarbon-substituted, α-oxy, and α-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.
AB - The direct application of carboxylic acids as a traceless activation group for radical Michael additions has been accomplished via visible light-mediated photoredox catalysis. Photon-induced oxidation of a broad series of carboxylic acids, including hydrocarbon-substituted, α-oxy, and α-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.
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U2 - 10.1021/ja505964r
DO - 10.1021/ja505964r
M3 - Article
C2 - 25032785
AN - SCOPUS:84905674432
VL - 136
SP - 10886
EP - 10889
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 31
ER -