Iron(II)-Catalyzed Asymmetric Intramolecular Aminohydroxylation of Indoles

被引:59
|
作者
Zhang, Yong-Qiang [1 ]
Yuan, Yong-An [1 ]
Liu, Guan-Sai [1 ]
Xu, Hao [1 ]
机构
[1] Georgia State Univ, Dept Chem, Atlanta, GA 30303 USA
关键词
ORGANOCATALYTIC ALPHA-AMINATION; ENANTIOSELECTIVE SYNTHESIS; COUPLING REACTIONS; IRON; AMINOOXYGENATION; LIGANDS; ALKENES; AZIRIDINATION; OXYAMINATION; EPOXIDATION;
D O I
10.1021/ol401666e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective intramolecular indole aminohydroxylation reaction is catalyzed by iron(II)-chiral bisoxazoline (BOX) complexes (ee up to 99%, dr>20:1). This discovery enables expedient asymmetric synthesis of a series of biologically active 3-amino oxindoles and 3-amino indolanes.
引用
收藏
页码:3910 / 3913
页数:4
相关论文
共 50 条
  • [21] Asymmetric aminohydroxylation of vinylfuran
    Bushey, ML
    Haukaas, MH
    O'Doherty, GA
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09): : 2984 - 2985
  • [22] Palladium-Catalyzed Asymmetric Aminohydroxylation of 1,3-Dienes
    Shen, Hong-Cheng
    Wu, Yu-Feng
    Zhang, Ying
    Fan, Lian-Feng
    Han, Zhi-Yong
    Gong, Liu-Zhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) : 2372 - 2376
  • [23] Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C-H Amination
    Bonnamour, Julien
    Bolm, Carsten
    ORGANIC LETTERS, 2011, 13 (08) : 2012 - 2014
  • [24] Asymmetric intramolecular alkylation of indoles with unactivated olefins.
    Han, XQ
    Widenhoefer, RA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U367 - U367
  • [25] A new approach to osmium-catalyzed asymmetric dihydroxylation and aminohydroxylation of olefins
    Andersson, MA
    Epple, R
    Fokin, VV
    Sharpless, KB
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (03) : 472 - 475
  • [26] Smaller substituents on nitrogen facilitate the osmium-catalyzed asymmetric aminohydroxylation
    Rudolph, J
    Sennhenn, PC
    Vlaar, CP
    Sharpless, KB
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24): : 2810 - 2813
  • [27] The Sharpless asymmetric aminohydroxylation
    Bodkin, JA
    McLeod, MD
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (24): : 2733 - 2746
  • [28] Asymmetric aminohydroxylation reaction
    Xu, YM
    Zhou, WS
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 1999, 19 (06) : 565 - 573
  • [29] Intramolecular iron(II)-catalyzed aminobromination of allyl N-tosyloxycarbamates
    Kamon, Takuma
    Shigeoka, Daisuke
    Tanaka, Tetsuaki
    Yoshimitsu, Takehiko
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (12) : 2363 - 2365
  • [30] Iron(II)-Catalyzed Asymmetric Epoxidation of Trisubstituted α,β-Unsaturated Esters
    Luo, Lan
    Yamamoto, Hisashi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (35) : 7803 - 7805