Transition metal-catalyzed iodine(III)-mediated nitrene transfer reactions: efficient tools for challenging syntheses

被引：154
作者：
Darses, B. [1 ]
Rodrigues, R. [1 ]
Neuville, L. [1 ]
Mazurais, M. [1 ]
Dauban, P. [1 ]
机构：
[1] Univ Paris Saclay, Univ Paris Sud, CNRS UPR 2301, Inst Chim Subst Nat, 1 Av Terrasse, F-91198 Gif Sur Yvette, France
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 03期
关键词：
C-H AMINATION; IMINOIODANE-MEDIATED AZIRIDINATION; CALCIUM SENSING RECEPTOR; STEREOSELECTIVE-SYNTHESIS; INTERMOLECULAR AMINATION; ALKENE AZIRIDINATION; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; INTRAMOLECULAR AMIDATION; C(SP(3))-H AMINATION;
D O I：
10.1039/c6cc07925c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The significant progress made in the area of transition metal-catalyzed nitrene transfer into C-H or C = C bonds mediated by iodine(III) oxidants has been translated into many elegant synthetic applications. This feature article summarizes the main total syntheses that take advantage of such reactions, thereby highlighting that catalytic C(sp(3))-H amination and alkene aziridination reactions have carved out their place in the organic chemist's toolbox.
引用
收藏
页码：493 / 508
页数：16
相关论文
共 121 条
  • [91] Selective Intermolecular Amination of C-H Bonds at Tertiary Carbon Centers
    Roizen, Jennifer L.
    Zalatan, David N.
    Du Bois, J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (43) : 11343 - 11346
  • [92] Metal-Catalyzed Nitrogen-Atom Transfer Methods for the Oxidation of Aliphatic C-H Bonds
    Roizen, Jennifer L.
    Harvey, Mark Edwin
    Du Bois, J.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 911 - 922
  • [93] Iminoiodane mediated aziridination of α-allylglycine:: access to a novel rigid arginine derivative and to the natural amino acid enduracididine
    Sanière, L
    Leman, L
    Bourguignon, JJ
    Dauban, P
    Dodd, RH
    [J]. TETRAHEDRON, 2004, 60 (28) : 5889 - 5897
  • [94] Transition-Metal-Catalyzed C-N Bond Forming Reactions Using Organic Azides as the Nitrogen Source: A Journey for the Mild and Versatile C-H Amination
    Shin, Kwangmin
    Kim, Hyunwoo
    Chang, Sukbok
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) : 1040 - 1052
  • [95] Total synthesis of the antitumor marine sponge alkaloid agelastatin A
    Stien, D
    Anderson, GT
    Chase, CE
    Koh, Y
    Weinreb, SM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) : 9574 - 9579
  • [96] Enantiospecific Total Synthesis of N-Methylwelwitindolinone D Isonitrile
    Styduhar, Evan D.
    Huters, Alexander D.
    Weires, Nicholas A.
    Garg, Neil K.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (47) : 12422 - 12425
  • [97] Total Synthesis of (-)-Kaitocephalin Based on a Rh-Catalyzed C-H Amination
    Takahashi, Keisuke
    Yamaguchi, Daisuke
    Ishihara, Jun
    Hatakeyama, Susumi
    [J]. ORGANIC LETTERS, 2012, 14 (06) : 1644 - 1647
  • [98] Synthesis of L-epi-Capreomycidine Derivatives via C-H Amination
    Tanino, Tetsuya
    Ichikawa, Satoshi
    Matsuda, Akira
    [J]. ORGANIC LETTERS, 2011, 13 (15) : 4028 - 4031
  • [99] Tanino Tetsuya, 2008, Nucleic Acids Symp Ser (Oxf), P557, DOI 10.1093/nass/nrn282
  • [100] Total Synthesis of (-)-Muraymycin D2 and Its Epimer
    Tanino, Tetsuya
    Ichikawa, Satoshi
    Shiro, Motoo
    Matsuda, Akira
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) : 1366 - 1377
45678910111213