Practical asymmetric synthesis of 1,2-diamines in the 3-aminoazepane series

被引:23
|
作者
Cutri, S
Bonin, M
Micouin, L
Husson, HP
Chiaroni, A
机构
[1] Univ Paris 05, Fac Sci Pharmaceut & Biol, F-75270 Paris 06, France
[2] Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
来源
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 07期
关键词
D O I
10.1021/jo026711s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and versatile method for the enantio- and diastereoselective synthesis of mono- or disubstituted 3-aminoazepanes is described. The key step involves a highly regio- and diastereoselective tandem ring-enlargement/alkylation or reduction process. This novel synthetic route provides enantiomerically pure constrained diamines interesting as scaffolds for medicinal chemistry.
引用
收藏
页码:2645 / 2651
页数:7
相关论文
共 50 条
  • [21] SYNTHESIS OF PRIMARY 1,2-DIAMINES BY HYDROGENATION OF ALPHA-AMINONITRILES
    FREIFELDER, M
    HASBROUCK, RB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (03) : 696 - 698
  • [22] Synthesis of new enantiomeric 1,2-diamines containing a myrtenyl fragment
    I. A. Dvornikova
    L. L. Frolova
    A. V. Kuchin
    I. P. Beletskaya
    Russian Journal of Organic Chemistry, 2007, 43 : 352 - 358
  • [23] Synthesis of 1,2-diamines from aziridines and iron carbonyl complexes
    Hancock, MT
    Pinhas, AR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U735 - U735
  • [24] Facile Synthesis of Bicyclic Amidines and Imidazolines from 1,2-Diamines
    Zhu, Qiang
    Lu, Yixin
    ORGANIC LETTERS, 2010, 12 (18) : 4156 - 4159
  • [25] Synthesis of new enantiomeric 1,2-diamines containing a myrtenyl fragment
    Dvornikova, I. A.
    Frolova, L. L.
    Kuchin, A. V.
    Beletskaya, I. P.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (03) : 352 - 358
  • [26] Chiral 1,2-amino alcohols and 1,2-diamines derived from cyclohexene oxide: Recent applications in asymmetric synthesis
    de Parrodi, Cecilia Anaya
    Juaristi, Eusebio
    SYNLETT, 2006, (17) : 2699 - 2715
  • [27] A convenient method for the preparation of 1,2-diamines
    Imagawa, K
    Hata, E
    Yamada, T
    Mukaiyama, T
    NIPPON KAGAKU KAISHI, 1997, (06) : 419 - 424
  • [28] STEREOSELECTIVITY OF HETEROCYCLIZATION OF 1,2-DIAMINES TO IMIDAZOLIDINES
    CHAPUIS, C
    GAUVREAU, A
    KLAEBE, A
    LATTES, A
    PERIE, JJ
    ROUSSEL, J
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE PARTIE II-CHIMIE MOLECULAIRE ORGANIQUE ET BIOLOGIQUE, 1973, (9-10): : 2676 - 2680
  • [29] Synthesis of 2-(trifluoroacetyl)chromones and their reactions with 1,2-diamines
    Irgashev, Roman A.
    Safrygin, Alexander V.
    Ezhikova, Marina A.
    Kodess, Mikhail I.
    Roeschenthaler, Gerd-Volker
    Sosnovskikh, Vyacheslav Y.
    TETRAHEDRON, 2015, 71 (12) : 1822 - 1830
  • [30] Synthesis of piperazinones and benzopiperazinones from 1,2-diamines and organoboronic acids
    Petasis, NA
    Patel, ZD
    TETRAHEDRON LETTERS, 2000, 41 (49) : 9607 - 9611