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

Research output: Contribution to journalArticle

264 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 languageEnglish (US)
Pages (from-to)10886-10889
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number31
DOIs
StatePublished - Aug 6 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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