Carboxylic acids as A traceless activation group for conjugate additions: A three-step synthesis of (±)-pregabalin

Lingling Chu; Chisa Ohta; Zhiwei Zuo; David W.C. MacMillan

doi:10.1021/ja505964r

Carboxylic acids as A traceless activation group for conjugate additions: A three-step synthesis of (±)-pregabalin

Lingling Chu, Chisa Ohta, Zhiwei Zuo, David W.C. MacMillan

Chemistry

Research output: Contribution to journal › Article › peer-review

279 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	10886-10889
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	31
DOIs	https://doi.org/10.1021/ja505964r
State	Published - Aug 6 2014

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja505964r

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title = "Carboxylic acids as A traceless activation group for conjugate additions: A three-step synthesis of (±)-pregabalin",

abstract = "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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AU - MacMillan, David W.C.

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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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