N-Cyanomethyl-β-chloroamines:: a convenient source of aziridinium ions

被引:23
作者
Couty, F [1 ]
Evano, G [1 ]
Prim, D [1 ]
机构
[1] Univ Versailles, CNRS, UMR 8086, SIRCOB, F-78035 Versailles, France
关键词
1,2-aminoethers; 1,2-diamines;
D O I
10.1016/j.tetlet.2005.02.016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Cyanomethyl-beta-chloroamines smoothly react with a range of alcohols or amines to give regio- and stereoselectively 1,2-aminoethers or 1,2-diamines. The reaction proceeds through the formation of an intermediate aziridinium ion. The N-cyanomethyl group can then be cleaved easily. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2253 / 2257
页数:5
相关论文
共 24 条
  • [1] The reactivity of the N-Boc protecting group:: an underrated feature
    Agami, C
    Couty, F
    [J]. TETRAHEDRON, 2002, 58 (14) : 2701 - 2724
  • [2] A straightforward synthesis of enantiopure 2-cyano azetidines from β-amino alcohols
    Agami, C
    Couty, F
    Evano, G
    [J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (03) : 297 - 302
  • [3] Amedjkouh M, 2001, CHEM-EUR J, V7, P4368, DOI 10.1002/1521-3765(20011015)7:20<4368::AID-CHEM4368>3.0.CO
  • [4] 2-K
  • [5] Reaction of aziridinium ions with organometallic reagents: optimization of the key step of ecopipam synthesis
    Andrews, DR
    Dahanukar, VH
    Eckert, JM
    Gala, D
    Lucas, BS
    Schumacher, DP
    Zavialov, IA
    [J]. TETRAHEDRON LETTERS, 2002, 43 (35) : 6121 - 6125
  • [6] Application of polydentate chiral amines within magnesium-mediated asymmetric deprotonation reactions
    Bassindale, MJ
    Crawford, JJ
    Henderson, KW
    Kerr, WJ
    [J]. TETRAHEDRON LETTERS, 2004, 45 (21) : 4175 - 4179
  • [7] Applications of aziridinium ions.: Selective syntheses of α,β-diamino esters, α-sulfanyl-β-amino esters, β-lactams, and 1,5-benzodiazepin-2-one
    Chuang, TH
    Sharpless, KB
    [J]. ORGANIC LETTERS, 2000, 2 (23) : 3555 - 3557
  • [8] Applications of aziridinium ions. selective syntheses of β-aryl-α,β-diamino esters
    Chuang, TH
    Sharpless, KB
    [J]. ORGANIC LETTERS, 1999, 1 (09) : 1435 - 1437
  • [9] Enantioselective rearrangement of a meso-cyclohexene oxide using norephedrine-derived chiral bases
    Colman, B
    de Sousa, SE
    O'Brien, P
    Towers, TD
    Watson, W
    [J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (21) : 4175 - 4182
  • [10] Expeditive synthesis of homochiral fused tri- and tetrazoles-piperazines from β-amino alcohols
    Couty, F
    Durrat, F
    Prim, D
    [J]. TETRAHEDRON LETTERS, 2004, 45 (19) : 3725 - 3728