Approach to pactamycin analogues using rhodium(II)-catalyzed alkene aziridination and C(sp3)-H amination reactions

被引:8
|
作者
Rodrigues, Romain [1 ]
Lazib, Yanis [1 ]
Maury, Julien [1 ,2 ]
Neuville, Luc [1 ]
Leboeuf, David [2 ]
Dauban, Philippe [1 ]
Darses, Benjamin [1 ]
机构
[1] Univ Paris Saclay, Univ Paris Sud, Inst Chim Subst Nat, CNRS,UPR 2301, 1 Ave Terrasse, F-91198 Gif Sur Yvette, France
[2] Univ Paris Saclay, Univ Paris Sud, Inst Chim Mol & Mat Orsay, CNRS,UMR 8182, Batiment 420, F-91405 Orsay, France
来源
ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 06期
关键词
C-H AMINATION; COPPER-CATALYZED AZIRIDINATION; 30S RIBOSOMAL-SUBUNIT; HIGHLY EFFICIENT; CORE FRAMEWORK; ANTITUMOR; BONDS; CYCLOPENTANE; CONSTRUCTION; ANTIBIOTICS;
D O I
10.1039/c7qo00878c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dirhodium(ii)-catalyzed nitrene transfers have been used to prepare a novel synthetic platform bearing the triamino moiety present in pactamycin, jogyamycin and cranomycin. Catalytic intramolecular C(sp(3))-H amination and alkene aziridination reactions, the latter followed by a nucleophilic aziridine ring opening, are the key steps of this strategy.
引用
收藏
页码:948 / 953
页数:6
相关论文
共 50 条
  • [1] Rhodium(II)-Catalyzed Selective C(sp3)-H Amination of Alkanes
    Boquet, Vincent
    Naves, Junio A. Guimaraes A.
    Brunard, Erwan
    Nasrallah, Ali
    Joigneaux, Mylene
    Carrizo, E. Daiann Sosa
    Saget, Tanguy
    Darses, Benjamin
    Sircoglou, Marie
    Dauban, Philippe
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (32)
  • [2] Intermolecular Rhodium(II)-Catalyzed Allylic C(sp3)-H Amination of Cyclic Enamides
    Rey-Rodriguez, Romain
    Jestin, Gregory
    Gandon, Vincent
    Grelier, Gwendal
    Retailleau, Pascal
    Darses, Benjamin
    Dauban, Philippe
    Gillaizeau, Isabelle
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (03) : 513 - 518
  • [3] Rhodium(II)-Catalyzed C(sp3)-H Diamination of Arylcyclobutanes
    Liu, Xinyu
    Wang, Zhifan
    Wang, Qiwei
    Wang, Yuanhua
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (30)
  • [4] Dirhodium(II)-Catalyzed C(sp3)-H Amination Using Iodine(III) Oxidants
    Buendia, Julien
    Grelier, Gwendal
    Dauban, Philippe
    ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 64, 2015, 64 : 77 - 118
  • [5] Rhodium-catalyzed intermolecular C(sp3)-H amination in a purely aqueous system
    Lu, Xunbo
    Shi, Yufeng
    Zhong, Fangrui
    GREEN CHEMISTRY, 2018, 20 (01) : 113 - 117
  • [6] Development of a Rhodium(II)-Catalyzed Chemoselective C(sp3)-H Oxygenation
    Lin, Yun
    Zhu, Lei
    Lan, Yu
    Rao, Yu
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (42) : 14937 - 14942
  • [7] Copper-Catalyzed sp3 C-H Amination
    Gephart, Raymond T., III
    Warren, Timothy H.
    ORGANOMETALLICS, 2012, 31 (22) : 7728 - 7752
  • [8] Progress in Enzyme-Catalyzed C(sp3)-H Amination
    Xu, Wei-Nan
    Gao, Ya-Dong
    Su, Ping
    Huang, Luqi
    He, Zhao-Lin
    Yang, Li-Cheng
    ACS CATALYSIS, 2024, 14 (18): : 14139 - 14160
  • [9] Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp2) H activation and C(sp3)-H amination
    Song, Liangliang
    Tian, Guilong
    Van der Eycken, Johan
    Van der Eycken, Erik V.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2019, 15 : 571 - 576
  • [10] Copper(II) ketimides in sp3 C-H amination
    Jayasooriya, Isuri U.
    Bakhoda, Abolghasem
    Palmer, Rachel
    Ng, Kristi
    Khachemoune, Nour L.
    Bertke, Jeffery A.
    Warren, Timothy H.
    CHEMICAL SCIENCE, 2021, 12 (47) : 15733 - 15738