Literature DB >> 30212610

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

Shengyang Ni1, Alberto F Garrido-Castro1, Rohan R Merchant1, Justine N de Gruyter1, Daniel C Schmitt2, James J Mousseau2, Gary M Gallego3, Shouliang Yang3, Michael R Collins3, Jennifer X Qiao4, Kap-Sun Yeung5, David R Langley5, Michael A Poss4, Paul M Scola5, Tian Qin1, Phil S Baran1.   

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.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amino acid synthesis; decarboxylative radical addition; library synthesis; redox-active esters; synthetic methods

Mesh：

Substances：

Year:  2018        PMID： 30212610      PMCID： PMC6352899          DOI： 10.1002/anie.201809310

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  46 in total

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2.  Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters.

Authors:  Melissa A Beenen; Daniel J Weix; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2006-05-17       Impact factor: 15.419

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4.  Solvent-controlled asymmetric Strecker reaction: stereoselective synthesis of alpha-trifluoromethylated alpha-amino acids.

Authors:  Hua Wang; Xiaoming Zhao; Youhua Li; Long Lu
Journal:  Org Lett       Date:  2006-03-30       Impact factor: 6.005

5.  Independence from the Sequence of Single-Electron Transfer of Photoredox Process in Redox-Neutral Asymmetric Bond-Forming Reaction.

Authors:  Tomohito Kizu; Daisuke Uraguchi; Takashi Ooi
Journal:  J Org Chem       Date:  2016-05-20       Impact factor: 4.354

6.  Asymmetric radical addition of ethers to enantiopure N-p-toluenesulfinyl aldimines, mediated by dimethylzinc-air.

Authors:  Tito Akindele; Yasutomo Yamamoto; Masaru Maekawa; Hiroyuki Umeki; Ken-ichi Yamada; Kiyoshi Tomioka
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

7.  The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.

Authors:  Martin J O'Donnell
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

8.  Synthesis and biological evaluation of (2S)- and (2R)-2-(3'-phosphonobicyclo[1.1.1]pentyl)glycines as novel group III selective metabotropic glutamate receptor ligands.

Authors:  Rosanna Filosa; Maura Marinozzi; Gabriele Costantino; Mette Brunsgaard Hermit; Christian Thomsen; Roberto Pellicciari
Journal:  Bioorg Med Chem       Date:  2006-02-03       Impact factor: 3.641

Review 9.  Control of asymmetry in the radical addition approach to chiral amine synthesis.

Authors:  Gregory K Friestad
Journal:  Top Curr Chem       Date:  2014

10.  Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids.

Authors:  Jie Wang; Tian Qin; Tie-Gen Chen; Laurin Wimmer; Jacob T Edwards; Josep Cornella; Benjamin Vokits; Scott A Shaw; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-06       Impact factor: 15.336
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  22 in total

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Authors:  Shengyang Ni; Natalia M Padial; Cian Kingston; Julien C Vantourout; Daniel C Schmitt; Jacob T Edwards; Monika M Kruszyk; Rohan R Merchant; Pavel K Mykhailiuk; Brittany B Sanchez; Shouliang Yang; Matthew A Perry; Gary M Gallego; James J Mousseau; Michael R Collins; Robert J Cherney; Pavlo S Lebed; Jason S Chen; Tian Qin; Phil S Baran
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Journal:  Org Lett       Date:  2020-09-17       Impact factor: 6.005

4.  Synthesis of Structurally Diverse 3-, 4-, 5-, and 6-Membered Heterocycles from Diisopropyl Iminomalonates and Soft C-Nucleophiles.

Authors:  Padmanabha V Kattamuri; Urmibhusan Bhakta; Surached Siriwongsup; Doo-Hyun Kwon; Lawrence B Alemany; Muhammed Yousufuddin; Daniel H Ess; László Kürti
Journal:  J Org Chem       Date:  2019-05-14       Impact factor: 4.354

5.  Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

Authors:  David J Charboneau; Haotian Huang; Emily L Barth; Cameron C Germe; Nilay Hazari; Brandon Q Mercado; Mycah R Uehling; Susan L Zultanski
Journal:  J Am Chem Soc       Date:  2021-11-30       Impact factor: 15.419

6.  Nickel-Catalyzed Reductive Alkylation of Heteroaryl Imines.

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7.  Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

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Journal:  J Am Chem Soc       Date:  2019-01-03       Impact factor: 15.419

8.  Synthesis of amino-diamondoid pharmacophores via photocatalytic C-H aminoalkylation.

Authors:  William K Weigel; Hoang T Dang; Hai-Bin Yang; David B C Martin
Journal:  Chem Commun (Camb)       Date:  2020-08-20       Impact factor: 6.222

9.  1,2-Difunctionalized bicyclo[1.1.1]pentanes: Long-sought-after mimetics for ortho/meta-substituted arenes.

Authors:  Jin-Xin Zhao; Yu-Xuan Chang; Chi He; Benjamin J Burke; Michael R Collins; Matthew Del Bel; Jeff Elleraas; Gary M Gallego; T Patrick Montgomery; James J Mousseau; Sajiv K Nair; Matthew A Perry; Jillian E Spangler; Julien C Vantourout; Phil S Baran
Journal:  Proc Natl Acad Sci U S A       Date:  2021-07-13       Impact factor: 11.205

10.  Preparation of α-amino acids via Ni-catalyzed reductive vinylation and arylation of α-pivaloyloxy glycine.

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Journal:  Chem Sci       Date:  2020-10-27       Impact factor: 9.825
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