A General Amino Acid Synthesis Enabled by Innate Radical Cross-Coupling

Angewandte Chemie
Shengyang NiPhil S Baran

Abstract

The direct union of primary, secondary, and tertiary carboxylic acids with a chiral glyoxylate-derived sulfinimine provides rapid access into a variety of enantiomerically pure α-amino acids (>85 examples). Characterized by operational simplicity, this radical-based reaction enables the modular assembly of exotic α-amino acids, including both unprecedented structures and those of established industrial value. The described method performs well in high-throughput library synthesis, and has already been implemented in three distinct medicinal chemistry campaigns.

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Citations

Jan 16, 2019·Organic & Biomolecular Chemistry·Sevan D HoustonCraig M Williams
Jan 25, 2019·Angewandte Chemie·Marc Montesinos-MagranerAbraham Mendoza
Sep 12, 2019·Chemical Communications : Chem Comm·Jianyang DongQingmin Wang
May 30, 2020·Organic & Biomolecular Chemistry·Hui FuChangwen Hu
Jul 24, 2020·Chemical Communications : Chem Comm·William K WeigelDavid B C Martin
Jun 27, 2019·Organic & Biomolecular Chemistry·Sevan D HoustonCraig M Williams
Aug 26, 2020·Angewandte Chemie·Francisco José Aguilar TroyanoAdrián Gómez-Suárez
Mar 14, 2021·Nature Communications·Marie L J WongEdward A Anderson
Jun 16, 2021·Journal of the American Chemical Society·Yang GaoPhil S Baran
Jun 26, 2021·Chemical Science·Andrey ShatskiyMarkus D Kärkäs
Jul 11, 2021·Proceedings of the National Academy of Sciences of the United States of America·Jin-Xin ZhaoPhil S Baran
Aug 10, 2021·Frontiers in Nutrition·Maria Bikaki, Nikolai Kuhnert
Mar 15, 2019·Organic Letters·Marie L J WongEdward A Anderson
Jul 11, 2020·The Journal of Organic Chemistry·Jiancheng WangYuehai Shen
Nov 23, 2018·Journal of the American Chemical Society·Jeishla L M MatosRyan A Shenvi
Apr 4, 2019·Journal of the American Chemical Society·Shengyang NiPhil S Baran
Sep 18, 2020·Organic Letters·Tao ShengPhil S Baran
Dec 12, 2019·Organic Letters·Alejandro Gómez-PalominoMercè Font-Bardia
Sep 29, 2019·Organic Letters·Stephen T J Cullen, Gregory K Friestad
Jan 4, 2019·Journal of the American Chemical Society·Cian KingstonPhil S Baran
Aug 27, 2021·The Journal of Organic Chemistry·Bin ZhaoBo Xu
Apr 10, 2020·The Journal of Organic Chemistry·Olivia Zhang, Jeffrey W Schubert
Jan 16, 2019·Organic Letters·Haruki InadaYoshihiko Yamamoto
Dec 1, 2021·Journal of the American Chemical Society·David J CharboneauSusan L Zultanski
Dec 14, 2021·Journal of the American Chemical Society·Jichao XiaoJohn Montgomery

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