Spontaneous symmetry breaking during interrupted crystallization of an axially chiral amino acid derivative

被引:12
|
作者
Sephton, Mark A. [1 ]
Emerson, Christopher R. [1 ]
Zakharov, Lev N. [1 ]
Blakemore, Paul R. [1 ]
机构
[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA
基金
美国国家科学基金会;
关键词
RACEMIC 1,1'-BINAPHTHYL; SPONTANEOUS RESOLUTION; CRYSTAL PHASE; SOLID-STATE; AUTOCATALYSIS; GENERATION; CATALYSTS; COMPLEX; MELT;
D O I
10.1039/b922028c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
High net enantiomeric excess was observed for crystal collections obtained by crystallization of the TFA salt of a configurationally stable yet racemic axially chiral amidoamine in EtOH solution with or without stirring (up to >99% ee at <= 15% crystallization).
引用
收藏
页码:2094 / 2096
页数:3
相关论文
共 50 条
  • [1] Chiral Symmetry Breaking of Axially Chiral Nicotinamide by Crystallization from the Melt
    Yagishita, Fumitoshi
    Okamoto, Kazuma
    Kamataki, Norifumi
    Kanno, Shota
    Mino, Takashi
    Kasashima, Yoshio
    Sakamoto, Masami
    CHEMISTRY LETTERS, 2013, 42 (12) : 1508 - 1510
  • [2] Spontaneous and Controlled Macroscopic Chiral Symmetry Breaking by Means of Crystallization
    Coquerel, Gerard
    Hoquante, Marine
    SYMMETRY-BASEL, 2020, 12 (11): : 1 - 17
  • [3] Breaking the symmetry of axially chiral N-aryl-2(1H)-pyrimidinones by spontaneous crystallization
    Sakamoto, M
    Utsumi, N
    Ando, M
    Saeki, M
    Mino, T
    Fujita, T
    Katoh, A
    Nishio, T
    Kashima, C
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (36) : 4360 - 4363
  • [4] Chiral symmetry breaking via crystallization of the glycine and α-amino acid system: a mathematical model
    Blanco, Celia
    Hochberg, David
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (28) : 12920 - 12934
  • [5] Complete chiral symmetry breaking of an amino acid derivative directed by circularly polarized light
    Noorduin, Wim L.
    Bode, Arno A. C.
    van der Meijden, Maarten
    Meekes, Hugo
    van Etteger, Albert F.
    van Enckevort, Willem J. P.
    Christianen, Peter C. M.
    Kaptein, Bernard
    Kellogg, Richard M.
    Rasing, Theo
    Vlieg, Elias
    NATURE CHEMISTRY, 2009, 1 (09) : 729 - 732
  • [6] Complete chiral symmetry breaking of an amino acid derivative directed by circularly polarized light
    Noorduin W.L.
    Bode A.A.C.
    Van Der Meijden M.
    Meekes H.
    Van Etteger A.F.
    Van Enckevort W.J.P.
    Christianen P.C.M.
    Kaptein B.
    Kellogg R.M.
    Rasing T.
    Vlieg E.
    Nature Chemistry, 2009, 1 (9) : 729 - 732
  • [7] Spontaneous symmetry breaking and chiral symmetry
    Li, LF
    PARTICLES AND FIELDS, 2000, 531 : 16 - 44
  • [8] Chiral symmetry breaking in unstirred crystallization
    Szurgot, M.
    CRYSTAL RESEARCH AND TECHNOLOGY, 2012, 47 (01) : 109 - 114
  • [9] SPONTANEOUS BREAKING OF CHIRAL SYMMETRY IN QCD
    DEALWIS, SP
    PHYSICS LETTERS B, 1979, 86 (01) : 67 - 71
  • [10] COMMENT ON SPONTANEOUS BREAKING OF CHIRAL SYMMETRY
    OHTSUBO, N
    TAMEIKE, S
    TAMURA, H
    YAMADA, E
    PROGRESS OF THEORETICAL PHYSICS, 1978, 60 (06): : 1849 - 1856