The synthesis of homochiral hybrid diamines derived from 1,1′-binaphthyl-2,2′-diamine and α-amino acids

被引:8
|
作者
Kowalczyk, B
Tarnowska, A
Weselinski, L
Jurczak, J
机构
[1] Warsaw Univ, Dept Organ Chem, PL-02093 Warsaw, Poland
[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
关键词
synthesis; binaphthyl moiety; homochiral diamines; diastereomers; axial chirality; amino acids;
D O I
10.1055/s-2005-872260
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient procedure for the preparation of homochiral diamines is presented. Coupling of racemic 1,1'-binaphthyl-2,2'-diamine with natural N-protected amino acids afforded the corresponding diastereomeric precursors which, following chromatographic separation and deprotection, gave the desired products in good yields. These compounds, called herein hybrid compounds, possess two different stereogenic elements, i.e., the centre containing the L-amino acid residues and the C-2 axis, resulting from the 1,1'-binaphthyl moiety.
引用
收藏
页码:2373 / 2375
页数:3
相关论文
共 50 条
  • [41] (R)-Di-tert-butyl 1,1′-binaphthyl-2,2′-dicarboxylate
    Thoss, Melanie
    Seidel, Ruediger W.
    Feigel, Martin
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O243 - U1433
  • [42] Dynamic Thermodynamic Resolution of Racemic 1,1′-Binaphthyl-2,2′-diol (BINOL)
    Shaashua, Omer
    Pollok, Dennis
    Dyadyuk, Alina
    Shames, Alexander I.
    Waldvogel, Siegfried R.
    Pappo, Doron
    ORGANIC LETTERS, 2024, 26 (10) : 2129 - 2134
  • [43] Di-tert-butyl (1,1′-binaphthyl-2,2′-dioxy)diacetate
    Mustafa, Asra
    Shah, Muhammad Raza
    Khatoon, Maimoona
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O912 - U3313
  • [44] Synthesis of optically active N,N,N′,N′-tetraphenyl-1,1'-binaphthyl-2,2'-diamine derivatives as analogues of BINAP
    Matsuzawa, Hiroshi
    Tanabe, Yoshiaki
    Miyake, Yoshihiro
    Nishibayashi, Yoshiaki
    ORGANOMETALLICS, 2008, 27 (15) : 4021 - 4024
  • [45] Practical synthetic protocols of enantiopure 1,1′-binaphthyl-2,2′-dicarboxylic acid and 2,2′-dicyano-1,1′-binaphthyl starting from optically active dibromide precursor
    Hoshi, T
    Nozawa, E
    Katano, M
    Suzuki, T
    Hagiwara, H
    TETRAHEDRON LETTERS, 2004, 45 (17) : 3485 - 3487
  • [46] Synthesis and Photochromic Reaction of 6,6′-Bis(diarylethenyl)-1,1′-binaphthyl-2,2′-diether
    Yamaguchi, Tadatsugu
    Takami, Shizuka
    CHEMISTRY LETTERS, 2022, 51 (06) : 610 - 613
  • [47] Synthesis and conformational study of (Bin)n and (β2,2-Bin)n homopeptides based on atropoisomeric α- and β-amino acids derived from 1,1'-binaphthyl
    Gaucher, Anne
    Dutot, Laurence
    Wright, Karen
    Wakselman, Michel
    Mazaleyrat, Jean-Paul
    Setnicka, Vladimir
    Kapitan, Josef
    Keiderling, Timothy A.
    Oancea, Simona
    Formaggio, Fernando
    Toniolo, Claudio
    Peptides 2004, Proceedings: BRIDGES BETWEEN DISCIPLINES, 2005, : 1015 - 1016
  • [48] Synthesis and Structural Characterization of a New Class of Strong Chiral Bronsted Acids: 1,1′-Binaphthyl-2,2′-bis(sulfuryl)imides (JINGLEs)
    Berkessel, Albrecht
    Christ, Philipp
    Leconte, Nicolas
    Neudoerfl, Joerg-M.
    Schaefer, Mathias
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (27) : 5165 - 5170
  • [49] Photophysical processes of a copolymer containing 1,1′-binaphthyl-2,2′-diamino and carbazolyl units
    Chen, ZB
    Zhang, CH
    Bai, FL
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2002, 58 (13) : 2885 - 2888
  • [50] catena-Poly[[trimethyltin(IV)]-μ-(1,1′-binaphthyl-2,2′-diyl phosphonato)]
    Wu, Jianjun
    Zhang, Rufen
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : M63 - U687