A selective reductive amination of aldehydes by the use of Hantzsch dihydropyridines as reductant

被引:103
|
作者
Itoh, T [1 ]
Nagata, K [1 ]
Miyazaki, M [1 ]
Ishikawa, H [1 ]
Kurihara, A [1 ]
Ohsawa, A [1 ]
机构
[1] Showa Univ, Sch Pharmaceut Sci, Shinagawa Ku, Tokyo, Japan
关键词
aldehyde; ketone; direct reductive amination; imine; Hantzsch dihydropyridine; scandium (III) triflate; Lewis acid;
D O I
10.1016/j.tet.2004.05.096
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct reductive amination of an aldehyde was carried out using a Hantzsch dihydropyridine as the reductant in the presence of a catalytic amount of scandium triflate. The reaction was highly selective towards aldehydes over ketones, and other reducible functional groups did not affect the reaction. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6649 / 6655
页数:7
相关论文
共 50 条
  • [1] Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant
    Wei, Duo
    Bruneau-Voisine, Antoine
    Valyaev, Dmitry A.
    Lugan, Noel
    Sortais, Jean-Baptiste
    CHEMICAL COMMUNICATIONS, 2018, 54 (34) : 4302 - 4305
  • [2] Isothiouronium Salts as Catalysts for the Direct Reductive Amination of Aldehydes with a Hantzsch Ester
    Lee, Haney
    Kang, Sungmin
    Kim, Taek Hyeon
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2018, 39 (04): : 575 - 578
  • [3] Reductive amination of aldehydes and ketones by a Hantzsch dihydropyridine using scandium triflate as a catalyst
    Itoh, T
    Nagata, A
    Kurihara, A
    Miyazaki, M
    Ohsawa, A
    TETRAHEDRON LETTERS, 2002, 43 (17) : 3105 - 3108
  • [4] Catalyst-free reductive amination of aromatic aldehydes with ammonium formate and Hantzsch ester
    Zhao, Pan-Pan
    Zhou, Xin-Feng
    Dai, Jian-Jun
    Xu, Hua-Jian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (45) : 9092 - 9096
  • [5] Use of sodium triacetoxyborohydride in reductive amination of ketones and aldehydes
    AbdelMagid, AF
    Maryanoff, CA
    REDUCTIONS IN ORGANIC SYNTHESIS: RECENT ADVANCES AND PRACTICAL APPLICATIONS, 1996, 641 : 201 - 216
  • [6] A review on the use of sodium triacetoxyborohydride in the reductive amination of ketones and aldehydes
    Abdel-Magid, Ahmed F.
    Mehrman, Steven J.
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (05) : 971 - 1031
  • [7] Au/TiO2 catalyzed reductive amination of aldehydes and ketones using formic acid as reductant
    Liang, Shengzong
    Monsen, Paige
    Hammond, Gerald B.
    Xu, Bo
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (04): : 505 - 509
  • [8] REDUCTIVE AMINATION OF PHOSPHONIC ALDEHYDES - A REEXAMINATION
    COLLIGNON, N
    FABRE, G
    VARLET, JM
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1981, 10 (01): : 81 - 86
  • [9] Reductive BOC-amination of aldehydes
    Bernacka, E
    Klepacz, A
    Zwierzak, A
    TETRAHEDRON LETTERS, 2001, 42 (30) : 5093 - 5094
  • [10] Reductive amination of tertiary anilines and aldehydes
    Lv, Yunhe
    Zheng, Yiying
    Li, Yan
    Xiong, Tao
    Zhang, Jingping
    Liu, Qun
    Zhang, Qian
    CHEMICAL COMMUNICATIONS, 2013, 49 (78) : 8866 - 8868