An alkoxide-directed intermolecular [2+2+1] annulation:: A three-component coupling reaction for the synthesis of tetrasubstituted α,β,-unsaturated γ-lactams

被引:46
|
作者
McLaughlin, Martin [1 ]
Takahashi, Masayuki [1 ]
Micalizio, Glenn C. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
alkynes; carbometalation; cross-coupling; imines; titanium;
D O I
10.1002/anie.200605060
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) In full control: A regio- and stereoselective cross-coupling reaction between internal alkynes and imines that provides selective access to allylic amines and γ-lactams has been developed (see scheme). This intermolecular [2+2+1] process could be described as an alkoxide-directed aza-Pauson-Khand-like annulation. The alkyne can tolerate a wide range of substituents R3. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3912 / 3914
页数:3
相关论文
共 50 条
  • [1] Pd-catalyzed three-component [2+2+1] cycloamination toward carbazoles
    Shen, Mingzhu
    Li, Min
    Yu, Jingxun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (16) : 3268 - 3272
  • [2] Three-Component Cascade Annulation of β-Ketothioamides Promoted by CF3CH2OH: A Regioselective Synthesis of Tetrasubstituted Thiophenes
    Wen, Li-Rong
    He, Tao
    Lan, Ming-Chao
    Li, Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21): : 10617 - 10628
  • [3] Me3SiCl-promoted three-component coupling reaction of a functionalized enamine, an acetal, and an alkyne:: An unprecedented approach to the synthesis of tetrasubstituted pyridines via a [3+2+1] intermolecular cyclization
    Sasada, Toshiaki
    Sakai, Norio
    Konakahara, Takeo
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6905 - 6908
  • [4] Synthesis of highly substituted 2-imidazolines through a three-component coupling reaction
    Han, Yao
    Xie, Yong-Xin
    Zhao, Lian-Biao
    Fan, Ming-Jin
    Liang, Yong-Min
    SYNTHESIS-STUTTGART, 2008, (01): : 87 - 93
  • [5] Highly efficient synthesis of tetrasubstituted 2,3-dihydropyrans by three-component 'one-pot' reaction
    Li, Chao
    Cai, Liang-Zhen
    Liu, Xiao-Dong
    Zhu, Shi-Zheng
    Xing, Chun-Hui
    Lu, Long
    TETRAHEDRON LETTERS, 2016, 57 (20) : 2171 - 2174
  • [6] Gold-catalyzed three-component annulation: An efficient synthesis of 1,2,3,5-tetrasubstituted dihydropyrazoles from alkynes, aldehydes, and hydrazines
    Suzuki, Yamato
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [7] Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling
    Davies, SG
    Smith, AD
    Cowley, AR
    SYNLETT, 2004, (11) : 1957 - 1960
  • [8] One-pot, three-component cascade synthesis of new tetrasubstituted pyrroles by coupling reaction of 2-functionally substituted 2-alkenals, amines, and nitroethane
    Keiko, Natalia A.
    Vchislo, Nadezhda V.
    Verochkina, Ekaterina A.
    Larina, Ludmila I.
    TETRAHEDRON, 2014, 70 (46) : 8959 - 8970
  • [9] Atom-economical synthesis of the functionalized spirocyclic oxindole-butenolide via three-component [2+2+1] cycloaddition strategy
    Li, Jian
    Liu, Yuejin
    Li, Chunju
    Jie, Haohua
    Jia, Xueshun
    GREEN CHEMISTRY, 2012, 14 (05) : 1314 - 1321
  • [10] A novel and facile method for the synthesis of 2,3-disubstituted Quinolines by a three-component coupling reaction
    Kikuchi, Satoshi
    Iwai, Masahiro
    Fukuzawa, Shin-Ichi
    SYNLETT, 2007, (17) : 2639 - 2642