Chiral crystallization of achiral organic compounds - Generation of chirality without chiral environment - (Part 1)

被引:42
作者
Koshima, H [1 ]
Matsuura, T
机构
[1] Ehime Univ, Fac Engn, Dept Appl Chem, Matsuyama, Ehime 7908577, Japan
[2] Kyoto Univ, Saikyou Ku, Kyoto 6158195, Japan
关键词
chiral crystallization; achiral molecules; X-ray crystallographic analysis; chiral space groups; generation of chirality; two-component molecular crystals; absolute asymmetric synthesis;
D O I
10.5059/yukigoseikyokaishi.56.268
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral crystallization of optically inactive (achiral) compounds such as benzophenone, phenol, phenanthrene, etc. has not been a commonly known phenomenon in organic chemistry. These compounds are known to crystallize to chiral crystals from their solutions. This review deals with this phenomenon, describing (1) what is chiral crystallization and how to find organic compounds undergoing chiral crystallization, (2) the preparation of chiral crystals from achiral organic compounds, (3) the characterization of chiral crystals, (4) the crystal structure of chiral crystals and the factors of the generation of chirality, (5) the chiral crystallization of two-component molecular compounds, (6) absolute asymmetric synthesis utilizing chiral crystallization, (7) other applications of chiral crystallization. Part 1 describes chapters (1), (2), (3), and (4).
引用
收藏
页码:268 / 279
页数:12
相关论文
共 63 条
[1]   Optical activity of oxo amide crystals [J].
Asahi, T ;
Nakamura, M ;
Kobayashi, J ;
Toda, F ;
Miyamoto, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (16) :3665-3669
[2]   TOTAL ASYMMETRIC TRANSFORMATION OF AN N-METHYLBENZAMIDE [J].
AZUMAYA, I ;
YAMAGUCHI, K ;
OKAMOTO, I ;
KAGECHIKA, H ;
SHUDO, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9083-9084
[3]   CHIRAL DISCRIMINATION OF COMPLEXES WITH D-3 SYMMETRY - SYNTHESIS AND CHARACTERIZATION OF TRIS(O,O'-BIS[(+)(S)-2-METHYLBUTYL] DITHIOPHOSPHATO)CHROMIUM(III) COMPLEXES (LAMBDA-DELTA)(CR[(+)(S)(S)MEBDTP](3)) AND LAMBDA-(-)(589)- AND DELTA-(+)(589)(CR[(+)(S)(S)MEBDTP](3)) AND CRYSTAL PACKING OF RACEMIC TRIS(O,O'-DIETHYL DITHIOPHOSPHATO)CHROMIUM(III), CR[DDTP](3) [J].
BISCARINI, P ;
FRANCA, R ;
KURODA, R .
INORGANIC CHEMISTRY, 1995, 34 (18) :4618-4626
[4]   The crystal structure of quinol Part II [J].
Caspari, WA .
JOURNAL OF THE CHEMICAL SOCIETY, 1927, :1093-1095
[5]  
CHOWDHURY PR, 1973, ACTA CRYSTALLOGR B, V29, P1362
[6]   CRYSTALLOGRAPHIC DATA FOR CARBAZOLE INDOLE AND PHENANTHRIDINE [J].
CLARKE, PT ;
SPINK, JM .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL CRYSTALLOGRAPHY AND CRYSTAL CHEMISTRY, 1969, B 25 :162-&
[7]   OPTICAL RESOLUTION BY DIRECT CRYSTALLIZATION OF ENANTIOMER MIXTURES [J].
COLLET, A ;
BRIENNE, MJ ;
JACQUES, J .
CHEMICAL REVIEWS, 1980, 80 (03) :215-230
[8]  
COLLET A, 1972, B SOC CHIM FR, P127
[9]  
DOCHERTY R, 1996, CRYSTAL GROWTH ORGAN, P2
[10]  
DONNAY JDH, 1983, CRYSTAL DATA DETERMI, V6