Photoinduced Kochi Decarboxylative Elimination for the Synthesis of Enamides and Enecarbamates from N-Acyl Amino Acids

被引:39
|
作者
Cartwright, Kaitie C. [1 ]
Lang, Simon B. [1 ]
Tunge, Jon A. [1 ]
机构
[1] Univ Kansas, Dept Chem, 2010 Malott Hall,1251 Wescoe Hall Dr, Lawrence, KS 66045 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 05期
基金
美国国家科学基金会;
关键词
ELECTRON-TRANSFER OXIDATION; ALKYL RADICALS; ISOMERIZATION; HYDROAMINATION; ALKENES; REDUCTION; AMIDES; ALLYLAMIDES; RUTHENIUM; AMINATION;
D O I
10.1021/acs.joc.9b00167
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Decarboxylative elimination of easily accessible N-acyl amino acids to provide enamide and enecarbamate building blocks has been realized through the combination of an organophotoredox catalyst and copper acetate as the terminal oxidant. This operationally simple process utilizes inexpensive and readily available reagents without preactivation of the carboxylic acid. Enamides and enecarbamates are now accessible directly from N-acyl amino acids consequently improving upon the utility of Kochi's oxidative decarboxylation of carboxylic acids.
引用
收藏
页码:2933 / 2940
页数:8
相关论文
共 50 条
  • [31] N-Acyl Amino Acids (Elmiric Acids): Endogenous Signaling Molecules with Therapeutic Potential
    Burstein, Sumner H.
    MOLECULAR PHARMACOLOGY, 2018, 93 (03) : 228 - 238
  • [32] THE THERMODYNAMICS OF IONIZATION OF AMINO ACIDS .2. THE IONIZATION CONSTANTS OF SOME N-ACYL AMINO ACIDS
    KING, EJ
    KING, GW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (06) : 1089 - 1099
  • [33] Preparation of N-acyl derivatives of amino acids from acyl chlorides and amino acids in the presence of cationic surfactants.: A variation of the Schotten-Baumann method of benzoylation of amino acids
    Jursic, BS
    Neumann, D
    SYNTHETIC COMMUNICATIONS, 2001, 31 (04) : 555 - 564
  • [34] Preparation of N-acyl derivatives of amino acids from acyl chlorides and amino acids in the presence of cationic surfactants:: A variation of the Schotten-Baumann method of benzolyation of amino acids.
    Jursic, BS
    Neumann, DM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U174 - U174
  • [35] INHIBITORY ACTION OF N-ACYL AMINO-ACIDS IN SEED-GERMINATION
    OMORI, M
    SUZUKI, T
    SAHASHI, Y
    YAMADA, K
    HASEGAWA, T
    AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1972, 36 (06): : A19 - +
  • [36] Identification of N-acyl amino acids that are positive allosteric modulators of glycine receptors
    Gallagher, Casey, I
    Sheipouri, Diba
    Shimmon, Susan
    Rawling, Tristan
    Vandenberg, Robert J.
    BIOCHEMICAL PHARMACOLOGY, 2020, 180
  • [37] N-Acyl Amino Acids: Metabolism, Molecular Targets, and Role in Biological Processes
    Battista, Natalia
    Bari, Monica
    Bisogno, Tiziana
    BIOMOLECULES, 2019, 9 (12)
  • [38] Ag-Catalyzed Practical Synthesis of N-Acyl Anthranilic Acids from Anthranils and Carboxylic Acids
    Wu, Changshu
    Gao, Yang
    Huo, Yanping
    Li, Xianwei
    Chen, Qian
    Hu, Xiao-Qiang
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (05): : 3150 - 3160
  • [39] INHIBITORY ACTION OF N-ACYL AMINO-ACIDS IN SEED-GERMINATION
    OMORI, M
    SAHASHI, Y
    SUZUKI, T
    YAMADA, K
    HASEGAWA, T
    JOURNAL OF THE AGRICULTURAL CHEMICAL SOCIETY OF JAPAN, 1972, 46 (05): : 219 - &
  • [40] MELTING BEHAVIOR OF SOME PURE N-ACYL AMINO-ACIDS AND PEPTIDES
    IYER, VN
    SHETH, GN
    SUBRAHMANYAM, VVR
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1982, 59 (07) : 856 - 859