Synthesis of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles from 1,2-amino alcohols

被引：45
作者：
Matsuoka, Yuki [1 ]
Ishida, Yasuhiro [1 ]
Sasaki, Daisuke [1 ]
Saigo, Kazuhiko [1 ]
机构：
[1] Univ Tokyo Hongo, Grad Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, Tokyo 1138656, Japan
来源：
TETRAHEDRON | 2006年 / 62卷 / 34期
关键词：
1,2-amino alcohol; chiral pool; cyclocondensation; enantiopure; N-substituted imidazole;
D O I：
10.1016/j.tet.2006.05.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly versatile method for the preparation of enantiopure 1-substituted, 1, 2-disubstituted, and 1,4,5-trisubstituted imidazoles was developed by using the cyclocondensation reaction of a 1,2-dicarbonyl compound, an aldehyde, a 1,2-amino alcohol, and ammonium acetate. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8199 / 8206
页数：8
相关论文
共 59 条
  • [1] Pyrimidinylimidazole inhibitors of p38: Cyclic N-1 imidazole substituents enhance p38 kinase inhibition and oral activity
    Adams, JL
    Boehm, JC
    Gallagher, TF
    Kassis, S
    Webb, EF
    Hall, R
    Sorenson, M
    Garigipati, R
    Griswold, DE
    Lee, JC
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (21) : 2867 - 2870
  • [2] Optically active aziridine esters by nucleophilic addition of nitrogen heterocycles to a chiral 2H-azirine-2-carboxylic ester
    Alves, MJ
    Fortes, AG
    Gonçalves, LF
    [J]. TETRAHEDRON LETTERS, 2003, 44 (33) : 6277 - 6279
  • [3] Arduengo III A. J, 2001, US Patent, Patent No. [6177575, 6,177,575 B1]
  • [4] Asymmetric lithium(I) and copper(II) alkoxy-N-heterocyclic carbene complexes;: crystallographic characterisation and Lewis acid catalysis
    Arnold, PL
    Rodden, M
    Davis, KM
    Scarisbrick, AC
    Blake, AJ
    Wilson, C
    [J]. CHEMICAL COMMUNICATIONS, 2004, (14) : 1612 - 1613
  • [5] One-pot synthesis of tetrasubstituted imidazoles catalyzed by zeolite HY and silica gel under microwave irradiation
    Balalaie, S
    Arabanian, A
    [J]. GREEN CHEMISTRY, 2000, 2 (06) : 274 - 276
  • [6] Synthesis of chiral ionic liquids from natural amino acids
    Bao, WL
    Wang, ZM
    Li, YX
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) : 591 - 593
  • [7] Intramolecular cycloadditions of nitrones derived from optically active 1-alkenyl-2-imidazolecarbaldehydes: regio- and diastereoselectivity
    Beccalli, E
    Broggini, G
    Contini, A
    De Marchi, I
    Zecchi, G
    Zoni, C
    [J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (20) : 3181 - 3187
  • [8] CARPENTER AJ, 1983, J CHEM RES-S, P1913
  • [9] Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis
    César, V
    Bellemin-Laponnaz, S
    Gade, LH
    [J]. CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) : 619 - 636
  • [10] 2,5-DILITHIATION OF N-PROTECTED IMIDAZOLES - SYNTHESES OF 2,5-DISUBSTITUTED DERIVATIVES OF 1-METHOXYMETHYL-IMIDAZOLE, 1-TRIPHENYLMETHYL-IMIDAZOLE, AND 1-(N,N-DIMETHYLSULPHONAMIDO)-IMIDAZOLE
    CHADWICK, DJ
    NGOCHINDO, RI
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (03): : 481 - 486
123456