Synthesis and characterization of chiral di(N-protected-α-amino)diazol-β-diketones from α-diazoketones and imidazolides derived from amino acids

被引:8
作者
Saraireh, Ibrahim A. M. [1 ]
机构
[1] Al Hussein Bin Talal Univ, Dept Chem, Maan, Jordan
关键词
Amino acid; Diazomethane; beta-Diketones; Carbonyldiimidazole; BETA-DIKETONES; AMINOACYLSILANES; HOMOLOGATION;
D O I
10.1016/j.tetlet.2012.01.093
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Di(N-protected-alpha-amino)diazo-beta-diketones were prepared by the reaction of activated N-protected-alpha-amino acids (imidazolides) with alpha-diazoketones, derived from natural amino acids, in the presence of lithium diisopropylamide in tetrahydrofuran as the solvent at -78 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2023 / 2025
页数:3
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共 15 条
  • [1] Chirality transfer in the aza-[2,3]-Wittig sigmatropic rearrangement
    Anderson, JC
    Ford, JG
    Whiting, M
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (20) : 3734 - 3748
  • [2] Stereoselective three-carbon and two-carbon elongation of the carbon chain in N-boc-protected α-aminoacylsilanes:: An entry to functionalized β-amino alcohols and to statine analogues
    Bonini, BF
    Comes-Franchini, M
    Fochi, M
    Laboroi, F
    Mazzanti, G
    Ricci, A
    Varchi, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (21) : 8008 - 8013
  • [3] Silylcupration of acylimidazolides:: a new synthesis of α-aminoacylsilanes and their synthetic applications
    Bonini, BF
    Comes-Franchini, M
    Fochi, M
    Mazzanti, G
    Ricci, A
    Varchi, G
    [J]. POLYHEDRON, 2000, 19 (05) : 529 - 531
  • [4] Synthesis of N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-protected (Fmoc) β-amino acids (= homo-α-amino acids) by direct homologation
    Ellmerer-Müller, EP
    Brössner, D
    Maslouh, N
    Takó, A
    [J]. HELVETICA CHIMICA ACTA, 1998, 81 (01) : 59 - 65
  • [5] SYNTHETIC STUDIES OF DIDEMNINS .2. APPROACHES TO STATINE DIASTEREOMERS
    HARRIS, BD
    BHAT, KL
    JOULLIE, MM
    [J]. TETRAHEDRON LETTERS, 1987, 28 (25) : 2837 - 2840
  • [6] SYNTHESIS OF N-PROTECTED ERYTHRO-PHENYLALANYLEPOXIDES
    HEINSOO, A
    RAIDARU, G
    LINASK, K
    JARV, J
    ZETTERSTROM, M
    LANGEL, U
    [J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (09) : 2245 - 2247
  • [7] Convenient and stereospecific homologation of N-fluorenyl-methoxycarbonyl-alpha-amino acids to their beta-homologues
    Leggio, A
    Liguori, A
    Procopio, A
    Sindona, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (13): : 1969 - 1971
  • [8] Highly practical methodology for the synthesis of D- and L-alpha-amino acids, N-protected alpha-amino acids, and N-methyl-alpha-amino acids
    Myers, AG
    Gleason, JL
    Yoon, T
    Kung, DW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (04) : 656 - 673
  • [9] Supercritical fluid extraction of cobalt with fluorinated and non-fluorinated beta-diketones
    Ozel, MZ
    Burford, MD
    Clifford, AA
    Bartle, KD
    Shadrin, A
    Smart, NG
    Tinker, ND
    [J]. ANALYTICA CHIMICA ACTA, 1997, 346 (01) : 73 - 80
  • [10] Improved Arndt-Eistert Synthesis of α-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger
    Pace, Vittorio
    Verniest, Guido
    Sinisterra, Josep-Vicent
    Alcantara, Andres R.
    De Kimpe, Norbert
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (16) : 5760 - 5763