Visible-Light-Promoted α-Benzylation of N-Phenyl α-Amino Acids to α-Amino Phenylpropanoids

被引:6
|
作者
Wang, Lin [1 ,2 ]
Li, Kang [1 ,2 ]
Ye, Tian [1 ,3 ]
Huang, Lei [1 ,3 ]
Wu, Huilan [1 ,2 ]
Zhang, Jingxuan [1 ,2 ]
Xie, Hongqi [1 ,3 ]
Liu, Yisong [1 ,3 ]
Zeng, Jianguo [1 ,3 ]
Cheng, Pi [1 ,3 ]
机构
[1] Hunan Agr Univ, Hunan Key Lab Tradit Chinese Vet Med, Changsha 410128, Hunan, Peoples R China
[2] Hunan Agr Univ, Coll Hort, Changsha 410128, Hunan, Peoples R China
[3] Hunan Agr Univ, Coll Vet Med, Changsha 410128, Hunan, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 16期
关键词
STREPTOMYCES SP TU-6075; PROTEASOME INHIBITORS; PHOTOREDOX CATALYSIS; ARYLOMYCIN-B; AMINO-ACIDS; SANGUINARINE; DERIVATIVES; HYPOCRELLIN; DOPA; CHELERYTHRINE;
D O I
10.1021/acs.joc.3c01196
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of & alpha;-amino phenylpropanoidsunder blue light-emitting diode irradiation has been developed through & alpha;-C-H benzylation of readily available N-phenylglycine ester with benzyl oxalates as a coupling partner under mildconditions. A range of N-phenyl glycine esters weresuccessfully converted to & alpha;-amino phenylpropanoid products inmoderate to good yields. The utility of this methodology is underlinedby its application to the late-state modification of natural products.
引用
收藏
页码:11924 / 11934
页数:11
相关论文
共 50 条
  • [21] Visible-Light-Promoted Intermolecular Oxidative Dearomatization of β-Naphthols with N-Hydroxycarbamates
    Cheng, Yuan-Zheng
    Zhou, Kai
    Zhu, Min
    Li, La-Ao-Chuan
    Zhang, Xiao
    You, Shu-Li
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (48) : 12519 - 12523
  • [22] Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process
    Wang, Rui
    Xie, Kai-jun
    Fu, Qiang
    Wu, Min
    Pan, Gao-feng
    Lou, Da-wei
    Liang, Fu-Shun
    ORGANIC LETTERS, 2022, 24 (10) : 2020 - 2024
  • [23] Visible-light-promoted oxidative halogenation of (hetero)arenes
    Lu, Lingling
    Li, Yiming
    Jiang, Xuefeng
    GREEN CHEMISTRY, 2020, 22 (18) : 5989 - 5994
  • [24] Visible-Light-Promoted Photocatalytic Hydrogen Production by Using an Amino-Functionalized Ti(IV) Metal-Organic Framework
    Horiuchi, Yu
    Toyao, Takashi
    Saito, Masakazu
    Mochizuki, Katsunori
    Iwata, Masatoshi
    Higashimura, Hideyuki
    Anpo, Masakazu
    Matsuoka, Masaya
    JOURNAL OF PHYSICAL CHEMISTRY C, 2012, 116 (39): : 20848 - 20853
  • [25] REACTIONS OF N-PHENYL ETHANOLAMINE WITH IMIDO PHOSPHITES AMIDO PHOSPHITES AND AMINO PHOSPHINES
    MITSUNOBU, O
    OHASHI, T
    KIKUCHI, M
    MUKAIYAM.T
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1966, 39 (02) : 214 - +
  • [26] Visible-light-promoted trifluoromethylselenolation of ortho-hydroxyarylenaminones
    Lu, Linghui
    Zhao, Xiongjie
    Dessie, Wubliker
    Xia, Xianwu
    Duan, Xiangjia
    He, Jun
    Wang, Rui
    Liu, Yu
    Wu, Chao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (08) : 1754 - 1758
  • [27] Visible-light-promoted phosphorylation carbonylation of unactivated alkenes
    Miao, Ren-Guan
    Wang, Yuanrui
    Wu, Xiao-Feng
    JOURNAL OF CATALYSIS, 2025, 442
  • [28] Lanthanide Luminescence in Visible-Light-Promoted Photochemical Reactions
    Barraza, Ramiro, Jr.
    Allen, Matthew J.
    MOLECULES, 2020, 25 (17):
  • [29] Visible-Light-Promoted Aerobic Homogenous Oxygenation Reactions
    Cheng, Xiaokai
    Hu, Xingen
    Lu, Zhan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (02) : 251 - 266
  • [30] SYNTHESIS AND MICROBIOLOGICAL EVALUATION OF ACETYLENIC AMINO ALCOHOLS N-PHENYL CARBAMATE DERIVATIVES
    Kassymova, M. K.
    Nauryzbayev, M. K.
    Mamyrbekova, A. K.
    Mamitova, A. D.
    Mamyrbekova
    Chechina, O. N.
    NEWS OF THE NATIONAL ACADEMY OF SCIENCES OF THE REPUBLIC OF KAZAKHSTAN-SERIES CHEMISTRY AND TECHNOLOGY, 2019, (04): : 43 - 48