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
  • [41] Manganese(I)-Catalyzed Regioselective C-H Allenylation: Direct Access to 2-Allenylindoles
    Lu, Qingquan
    Gressies, Steffen
    Klauck, Felix J. R.
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (23) : 6660 - 6664
  • [42] Rhodium(III)-catalyzed C-H/C-C activation sequence: vinylcyclopropanes as versatile synthons in direct C-H allylation reactions
    Wu, Jia-Qiang
    Qiu, Zhi-Ping
    Zhang, Shang-Shi
    Liu, Jing-Gong
    Lao, Ye-Xing
    Gu, Lian-Quan
    Huang, Zhi-Shu
    Li, Juan
    Wang, Honggen
    CHEMICAL COMMUNICATIONS, 2015, 51 (01) : 77 - 80
  • [43] Ruthenium-Catalyzed C-H Allylation of Alkenes with Allyl Alcohols via C-H Bond Activation in Aqueous Solution
    Wu, Xiaowei
    Ji, Haitao
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19): : 12094 - 12102
  • [44] Cobalt(III)-Catalyzed Allylation with Allyl Acetates by C-H/C-O Cleavage
    Moselage, Marc
    Sauermann, Nicolas
    Koeller, Julian
    Liu, Weiping
    Gelman, Dmitri
    Ackermann, Lutz
    SYNLETT, 2015, 26 (11) : 1596 - 1600
  • [45] Palladium-catalyzed direct C-H allylation of arenes without directing groups
    Ying, Cheng-Hao
    Duan, Wei-Liang
    Organic Chemistry Frontiers, 2014, 1 (05): : 546 - 550
  • [46] Mild Rhodium(III)-Catalyzed Direct C-H Allylation of Arenes with Allyl Carbonates
    Wang, Honggen
    Schroeder, Nils
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (20) : 5386 - 5389
  • [47] Rhodium(III)-catalyzed directed C-H benzylation and allylation of indoles with organosilicon reagents
    Lu, Ming-Zhu
    Wang, Cheng-Qiang
    Song, Sheng-Jin
    Loh, Teck-Peng
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02): : 303 - 307
  • [48] Iron-Catalyzed para-Selective C-H Allylation of Aniline Derivatives
    You, Qiulin
    Xiao, Xin
    Shi, Yang
    Wu, Yimin
    Tan, Guangying
    ORGANIC LETTERS, 2023, 25 (42) : 7683 - 7688
  • [49] Ruthenium(II)-Catalyzed S(II)-Directed Aromatic C-H Allylation with Vinylaziridines
    Duan, Yu-Tong
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (23): : 16076 - 16090
  • [50] Mechanistic exploration of Rh(III)-catalyzed C-H allylation of benzamides with allyl bromide
    Pal, Poulami
    Mondal, Sonjoy
    Chatterjee, Arpita
    Saha, Rohini
    Chakrabarty, Kuheli
    Das, GourabKanti
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2021, 949
12345