Highly diastereoselective aminoalkylation of naphthols with chiral amines mediated by lithium perchlorate solution in diethyl ether

被引:47
作者
Saidi, MR [1 ]
Azizi, N [1 ]
机构
[1] Sharif Univ Technol, Dept Chem, Tehran, Iran
关键词
D O I
10.1016/S0957-4166(02)00863-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
One-pot, three-component, Mannich reaction of naphthols with in situ prepared imines in 5 M ethereal lithium perchlorate at room temperature affords the corresponding aminoalkylated products in high yields with high diastereoselectivities. The process is exemplified by the reaction of 2-naphthol with (R)-1-phenylethylamine and an aromatic aldehyde in concentrated ethereal lithium perchlorate solution, which affords a highly diastereoselective access to the requisite 2-aminoalkylated product. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:389 / 392
页数:4
相关论文
共 25 条
  • [1] AIDI MR, 1997, J CHEM SOC P1, P1983
  • [2] [Anonymous], 1991, COMPREHENSIVE ORGANI
  • [3] Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
  • [4] 2-E
  • [5] Use of readily available chiral compounds related to the Betti base in the enantioselective addition of diethylzinc to aryl aldehydes
    Cardellicchio, C
    Ciccarella, G
    Naso, F
    Perna, F
    Tortorella, P
    [J]. TETRAHEDRON, 1999, 55 (51) : 14685 - 14692
  • [6] Chi KW, 1999, B KOREAN CHEM SOC, V20, P973
  • [7] Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: Stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation
    Cimarelli, C
    Mazzanti, A
    Palmieri, G
    Volpini, E
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) : 4759 - 4765
  • [8] Alkylation of dianions derived from 2-(1-iminoalkyl) phenols: Synthesis of functionalized 2-acyl phenols.
    Cimarelli, C
    Palmieri, G
    [J]. TETRAHEDRON, 1998, 54 (51) : 15711 - 15720
  • [9] Grumbach HJ, 1996, SYNTHESIS-STUTTGART, P883
  • [10] Amino(hetero)arylmethylation of phenols with N-[α-amino(hetero)arylmethyl]benzotriazoles
    Katritzky, AR
    Abdel-Fattah, AAA
    Tymoshenko, DO
    Belyakov, SA
    Ghiviriga, I
    Steel, PJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) : 6071 - 6075