Rh2(II)-Catalyzed Ester Migration to Afford 3H-Indoles from Trisubstituted Styryl Azides

被引：35
作者：
Kong, Chen [1 ]
Driver, Tom G. [1 ]
机构：
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
来源：
ORGANIC LETTERS | 2015年 / 17卷 / 04期
基金：
美国国家科学基金会;
关键词：
C-H AMINATION; FISCHER INDOLIZATION APPROACH; BOND AMINATION; TRANSLATION INITIATION; CASCADE REACTIONS; ARYL AZIDES; NAZAROV ELECTROCYCLIZATION; STEREOSELECTIVE-SYNTHESIS; CLAISEN REARRANGEMENT; OLEFIN AZIRIDINATION;
D O I：
10.1021/ol503541z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rh-2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4 pi-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the beta-styryl substituent.
引用
收藏
页码：802 / 805
页数：4
相关论文
共 112 条
  • [1] Inhibition of Translation Initiation as a Novel Paradigm for Cancer Therapy
    Aktas, Bertal H.
    Halperin, Jose A.
    Wagner, Gerhard
    Chorev, Michael
    [J]. ANNUAL REPORTS IN MEDICINAL CHEMISTRY, VOL 46, 2011, 46 : 189 - 210
  • [2] Diastereoselective Access to Tri- and Pentacyclic Spiro-γ-lactam-oxindole Cores through a Tandem Aza-Michael Initiated Ring Closure Sequence
    Allous, Iyad
    Comesse, Sebastien
    Sanselme, Morgane
    Daich, Adam
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (27) : 5303 - 5310
  • [3] Alper PB, 1999, ANGEW CHEM INT EDIT, V38, P3186, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3186::AID-ANIE3186>3.3.CO
  • [4] 2-5
  • [5] Orthogonal Pd- and Cu-based catalyst systems for C- and N-arylation of oxindoles
    Altman, Ryan A.
    Hyde, Alan M.
    Huang, Xiaohua
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9613 - 9620
  • [6] Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl Sulfides with tert-butoxycarbonyl azide.: Access to N-allenylsulfenimides
    Bacci, JP
    Greenman, KL
    Van Vranken, DL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) : 4955 - 4958
  • [7] Fe(II)-catalyzed imidation of allyl sulfides and subsequent [2,3]-sigmatropic rearrangement.: Preparation of α-branched N-tert-butyloxycarbonyl (Boc)-protected N-Allylamines
    Bach, T
    Körber, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) : 2358 - 2367
  • [8] Iron(II)-mediated nitrene transfer from t-butyloxycarbonyl azide (BocN3) to sulfoxides, sulfides, and ketene acetals
    Bach, T
    Körber, C
    [J]. TETRAHEDRON LETTERS, 1998, 39 (28) : 5015 - 5016
  • [9] Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages
    Barral, Karine
    Moorhouse, Adam D.
    Moses, John E.
    [J]. ORGANIC LETTERS, 2007, 9 (09) : 1809 - 1811
  • [10] Highly diastereoselective cycloisomerization of acyclic trienones. The interrupted Nazarov reaction
    Bender, JA
    Blize, AE
    Browder, CC
    Giese, S
    West, FG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) : 2430 - 2431
12345678910