Decarbonylative Radical Coupling of α-Aminoacyl Tellurides: Single-Step Preparation of γ-Amino and α,β-Diamino Acids and Rapid Synthesis of Gabapentin and Manzacidin A†
Dr. Masanori Nagatomo
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorHayato Nishiyama
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorHaruka Fujino
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Masayuki Inoue
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)Search for more papers by this authorDr. Masanori Nagatomo
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorHayato Nishiyama
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorHaruka Fujino
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorCorresponding Author
Prof. Dr. Masayuki Inoue
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)Search for more papers by this authorThis research was financially supported by the Funding Program for Next Generation World-Leading Researchers (JSPS), a Grant-in-Aid for Scientific Research (A) to M.I., and a Grant-in-Aid for Young Scientists (B) (JSPS) to M.N.
Abstract
A new radical-based coupling method has been developed for the single-step generation of various γ-amino acids and α,β-diamino acids from α-aminoacyl tellurides. Upon activation by Et3B and O2 at ambient temperature, α-aminoacyl tellurides were readily converted into α-amino carbon radicals through facile decarbonylation, which then reacted intermolecularly with acrylates or glyoxylic oxime ethers. This mild and powerful method was effectively incorporated into expeditious synthetic routes to the pharmaceutical agent gabapentin and the natural product (−)-manzacidin A.
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