Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin | Zendy

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

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Carboxylic Acids as A Traceless Activation Group for Conjugate Additions: A Three-Step Synthesis of (±)-Pregabalin

Author(s) -

Lingling Chu,

Chisa Ohta,

Zhiwei Zuo,

David W. C. MacMillan

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja505964r

Subject(s) - chemistry , conjugate , michael reaction , combinatorial chemistry , catalysis , group (periodic table) , pregabalin , carboxylate , organic chemistry , psychology , mathematical analysis , mathematics , psychotherapist

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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