Supramolecular architecture consisting of an enantiopure amine and an achiral carboxylic acid: Application to the enantioseparation of racemic alcohols

被引：38

作者：

Kobayashi, Y ^{[1
]}

Kodama, K ^{[1
]}

Saigo, K ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Engn, Dept Chem & Biotechnol, Bunkyo Ku, Tokyo 1138656, Japan

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 17期

关键词：

D O I：

10.1021/ol048948b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three-dimensionally dissymmetric cavities are created from an enantiopure amine and an achiral carboxylic acid, which can incorporate the third components to realize the formation of closely packed crystals. The combination demonstrates enantioselective inclusion for 20 kinds of racemic alcohols. The inclusion phenomenon occurs not only during crystallization but also in the solid state.

引用

页码：2941 / 2944

页数：4

共 17 条

[1] Modular chemistry: Secondary building units as a basis for the design of highly porous and robust metal-organic carboxylate frameworks [J].

Eddaoudi, M ;

Moler, DB ;

Li, HL ;

Chen, BL ;

Reineke, TM ;

O'Keeffe, M ;

Yaghi, OM .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (04) :319-330

[2] PREPARATION, CLATHRATION ABILITY, AND CATALYSIS OF A 2-DIMENSIONAL SQUARE NETWORK MATERIAL COMPOSED OF CADMIUM(II) AND 4,4'-BIPYRIDINE [J].

FUJITA, M ;

KWON, YJ ;

WASHIZU, S ;

OGURA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (03) :1151-1152

[3]

Hagrman PJ, 1999, ANGEW CHEM INT EDIT, V38, P2639

[4] Cation control of pore and channel size in cage-based metal-organic porous materials [J].

Harrison, RG ;

Fox, OD ;

Meng, MO ;

Dalley, NK ;

Barbour, LJ .

INORGANIC CHEMISTRY, 2002, 41 (04) :838-843

[5] Systematic study of chiral discrimination upon crystallisation. Part 2. Chiral discrimination of 2-arylalkanoic acids by (1R,2S)-2-amino-1,2-diphenylethanol [J].

Kinbara, K ;

Kobayashi, Y ;

Saigo, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (08) :1767-1775

[6] Chiral discrimination of 2-arylalkanoic acids by (1S,2R)-1-aminoindan-2-ol through the formation of a consistent columnar supramolecular hydrogen-bond network [J].

Kinbara, K ;

Kobayashi, Y ;

Saigo, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (01) :111-119

[7] Crystal structures of the salts of chiral primary amines with achiral carboxylic acids: Recognition of the commonly-occurring supramolecular assemblies of hydrogen-bond networks and their role in the formation of conglomerates [J].

Kinbara, K ;

Hashimoto, Y ;

Sukegawa, M ;

Nohira, H ;

Saigo, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) :3441-3449

[8] Chiral discrimination upon crystallisation of the diastereomeric salts of 1-arylethylamines with mandelic acid or p-methoxymandelic acid: Interpretation of the resolution efficiencies on the basis of the crystal structures [J].

Kinbara, K ;

Sakai, K ;

Hashimoto, Y ;

Nohira, H ;

Saigo, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (12) :2615-2622

[9] Design and synthesis of an exceptionally stable and highly porous metal-organic framework [J].

Li, H ;

Eddaoudi, M ;

O'Keeffe, M ;

Yaghi, OM .

NATURE, 1999, 402 (6759) :276-279

[10]

MICHI J, 1995, MODULAR CHEM

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