Manganese(I)-Catalyzed C-H Allylation of Tryptophans and Their Oligopeptides On Water

被引：1
|
作者：
Struwe, Julia [1 ]
Oyama, Tsuyoshi [1 ]
Gallou, Fabrice [2 ]
Ackermann, Lutz [1 ,3 ]
机构：
[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, Wohler Forschungsinst Nachhaltige Chem, Tammannstr 2, D-37077 Gottingen, Germany
[2] Novartis Pharm AG, Chem & Analyt Dev, CH-4056 Basel, Switzerland
[3] German Ctr Cardiovasc Res DZHK, Potsdamer Str 58, D-10785 Berlin, Germany
来源：
SYNLETT | 2024年 / 35卷 / 08期
关键词：
C-H activation; on water; peptides; manganese catalysis; late-stage functionalization; BOND FUNCTIONALIZATION; CROSS-COUPLINGS; AMINO-ACIDS; ACTIVATION; ARYLATION; CHALLENGES; CATALYSIS; PEPTIDES;
D O I：
10.1055/a-2268-4678
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The manganese(I)-catalyzed allylation of the amino acid tryptophan is realized under exceedingly mild conditions using water as a sustainable and non-hazardous reaction medium, instead of classical organic solvents, with great potential for green and sustainable chemis-try. Synthetically useful alpha,beta-unsaturated esters can be accessed by reaction with Morita-Baylis-Hillman (MBH) adducts following a fast C-H activation approach. The robustness of this procedure is reflected by kinetic analysis at different reaction temperatures and reduced catalyst loadings are employed.
引用
收藏
页码：903 / 907
页数：5
相关论文
共 50 条
  • [21] Ruthenium-catalyzed C-H allylation of arenes with allylic amines
    Yan, Rui
    Wang, Zhong-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (21) : 3961 - 3969
  • [22] Palladium-Catalyzed ortho C-H Allylation of Tertiary Anilines
    Yuan, Chunchen
    Zhang, Wenlong
    ORGANIC LETTERS, 2025,
  • [23] Cobalt-Catalyzed C-H Allylation of Arenes with Allylic Amines
    Yan, Rui
    Yu, Hang
    Wang, Zhong-Xia
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (05) : 1205 - 1210
  • [24] Rh(III)-Catalyzed C-H Allylation of Aromatic Ketoximes with Vinylaziridines
    Nie, Jing-Jing
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (08): : 5764 - 5777
  • [25] Low-valent cobalt-catalyzed C-H allylation
    Cong, Xuefeng
    Zhai, Shengxian
    Zeng, Xiaoming
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (06): : 673 - 677
  • [26] DFT Case Study on the Comparison of Ruthenium-Catalyzed C-H Allylation, C-H Alkenylation, and Hydroarylation
    Zhang, Lei
    Wang, Ling-Ling
    Fang, De-Cai
    ACS OMEGA, 2022, 7 (07): : 6133 - 6141
  • [27] Manganese-Catalyzed C-H Olefination Reactions
    Hu, Yuanyuan
    Wang, Congyang
    CHEMCATCHEM, 2019, 11 (04) : 1167 - 1174
  • [28] Manganese(I)-Catalyzed C-H 3,3-Difluoroallylation of Pyridones and Indoles
    Ni, Jiabin
    Zhao, Hongchuan
    Zhang, Ao
    ORGANIC LETTERS, 2017, 19 (12) : 3159 - 3162
  • [29] D Manganese(II/III/I)-Catalyzed C-H Arylations in Continuous Flow
    Zhu, Cuiju
    Oliveira, Joao C. A.
    Shen, Zhigao
    Huang, Huawen
    Ackermann, Lutz
    ACS CATALYSIS, 2018, 8 (05): : 4402 - 4407
  • [30] CoIII-Catalyzed C-H Alkenylation and Allylation with Cyclopropenes via Sequential C-H/C-C Bond Activation
    Kim, Ye Lim
    Park, Sun-a
    Choi, Seoung-Mi
    Park, Jong-Un
    Kim, Ju Hyun
    ORGANIC LETTERS, 2021, 23 (17) : 6674 - 6679
12345