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
  • [31] Synthesis and conformational studies of a chiral octadentate ligand derived from (R)-1,1′-binaphthyl-2,2′-diamine and its dinuclear zinc(II) and nickel(II) complexes
    Mimmi, MC
    Gullotti, M
    Santagostini, L
    Pagliarin, R
    De Gioia, L
    Monzani, E
    Casella, L
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2003, (21) : 3934 - 3944
  • [33] Experimental and Density Functional Theory Calculation Studies on Raman and Infrared Spectra of 1,1′-Binaphthyl-2,2′-diamine
    Zhang, Zhen-lin
    Wang, Wen-lou
    Liu, Shi-lin
    Chen, Dong-ming
    CHINESE JOURNAL OF CHEMICAL PHYSICS, 2017, 30 (01) : 7 - 15
  • [34] Kinetic resolution of 1,1′-binaphthyl-2,2′-diamine derivatives by chiral calcium phosphate-catalyzed acylation
    Uchikura, Tatsuhiro
    Kanno, Yuki
    Fukuda, Yukino
    Sato, Mikoto
    Akiyama, Takahiko
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (17) : 3444 - 3447
  • [35] Structure and Enantio-Differentiating Behaviors of Nickel(II) Complexes with Chiral Schiff Base Ligands Derived from 1,1′-Binaphthyl-2,2′-diamine
    Saito, Mariko
    Sato, Hisako
    Mori, Yukie
    Fukuda, Yutaka
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2009, 82 (10) : 1266 - 1273
  • [36] Mono- and dinuclear complexes of chiral tri- and tetradentate Schiff-base ligands derived from 1,1′-binaphthyl-2,2′-diamine
    Telfer, SG
    Sato, T
    Harada, T
    Kuroda, R
    Lefebvre, J
    Leznoff, DB
    INORGANIC CHEMISTRY, 2004, 43 (20) : 6168 - 6176
  • [37] 1,1′-Binaphthyl-2,2′-diol and 2,2′-diamino-1,1′-binaphthyl:: versatile frameworks for chiral ligands in coordination and metallosupramolecular chemistry
    Telfer, SG
    Kuroda, R
    COORDINATION CHEMISTRY REVIEWS, 2003, 242 (1-2) : 33 - 46
  • [38] Synthesis of 1,1′-binaphthyl-2,2′-diyl phosphoroselenoic amides and their conversion to optically pure phosphoramidites
    Murai, Toshiaki
    Inaji, Shinsuke
    Morishita, Ken
    Shibahara, Fumitoshi
    Tokunaga, Makoto
    Obora, Yasushi
    Tsuji, Yasushi
    CHEMISTRY LETTERS, 2006, 35 (12) : 1424 - 1425
  • [39] 1,1′-binaphthyl-2,2′-diamine as a novel MALDI matrix to enhance the in situ imaging of metabolic heterogeneity in lung cancer
    Sun, Chenglong
    Liu, Wei
    Mu, Yan
    Wang, Xiao
    TALANTA, 2020, 209
  • [40] A new chiral bithiophene based on derivatization of 1,1′-binaphthyl-2,2′-diol
    Drabowicz, J.
    Krasowska, D.
    Mielniczak, A.
    POLISH JOURNAL OF CHEMISTRY, 2007, 81 (11) : 1983 - 1985