Chiral recognition of amino acid derivatives by 1,1'-binaphthalene-8,8'-diol

被引：17

作者：

Kawabata, T ^{[1
]}

Kuroda, A ^{[1
]}

Nakata, E ^{[1
]}

Takasu, K ^{[1
]}

Fuji, K ^{[1
]}

机构：

[1] KYOTO UNIV,INST CHEM RES,UJI,KYOTO 611,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 24期

关键词：

D O I：

10.1016/0040-4039(96)00702-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active 1,1'-binaphthalene-8,8'-diol is found to bind a variety of amines in CDCl3 or C6D6 solution. Significant chiral recognition (Delta Delta G degrees = similar to 1.2 kcal/mol) was observed in the valine derivative 4. A three-point binding motif is assumed. (C) 1996 Elsevier Science Ltd

引用

收藏

页码：4153 / 4156

页数：4

相关论文

共 18 条

[1] CHIRAL RECOGNITION IN CLEFTS AND CYCLOPHANE CAVITIES SHAPED BY THE 1,1'-BINAPHTHYL MAJOR GROOVE [J].

CASTRO, PP ;

GEORGIADIS, TM ;

DIEDERICH, F .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5835-5838

[2] AN INTERNAL COORDINATE MONTE-CARLO METHOD FOR SEARCHING CONFORMATIONAL SPACE [J].

CHANG, G ;

GUIDA, WC ;

STILL, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4379-4386

[3] A WIDELY APPLICABLE METHOD OF RESOLUTION OF BINAPHTHYLS - PREPARATION OF ENANTIOMERICALLY PURE 1,1'-BINAPHTHALENE-2,2'-DIOL, 1,1'-BINAPHTHALENE-2,2'-DITHIOL, 2'-MERCAPTO-1,1'-BINAPHTHALENE-2-OL, AND 1,1'-BINAPHTHALENE-8,8'-DIOL [J].

FABBRI, D ;

DELOGU, G ;

DELUCCHI, O .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6599-6601

[4] SYNTHESIS AND BINDING-PROPERTIES OF A PEPTIDE RECEPTOR [J].

FLACK, SS ;

KILBURN, JD .

TETRAHEDRON LETTERS, 1995, 36 (19) :3409-3412

[5] ENANTIOSELECTIVE PROTONATION OF ENOLATES - NOVEL CHIRAL PROTON SOURCES AND REMARKABLE EFFECTS OF THE COUNTERCATION [J].

FUJI, K ;

KAWABATA, T ;

KURODA, A ;

TAGA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :1914-1915

[6] PALLADIUM(II)-DIRECTED ASSEMBLY OF MACROCYCLIC DINUCLEAR COMPLEXES COMPOSED OF (EN)PD2+ AND BIS(4-PYRIDYL)-SUBSTITUTED BIDENTATE LIGANDS - REMARKABLE ABILITY FOR MOLECULAR RECOGNITION OF ELECTRON-RICH AROMATIC GUESTS [J].

FUJITA, M ;

NAGAO, S ;

IIDA, M ;

OGATA, K ;

OGURA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1574-1576

[7] A RECEPTOR FOR THE ENANTIOSELECTIVE RECOGNITION OF PHENYLALANINE AND TRYPTOPHAN UNDER NEUTRAL CONDITIONS [J].

GALAN, A ;

ANDREU, D ;

ECHAVARREN, AM ;

PRADOS, P ;

DEMENDOZA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1511-1512

[8] CHIRAL RECOGNITION OF TARTARIC ACID-DERIVATIVES BY A SYNTHETIC RECEPTOR [J].

GARCIATELLADO, F ;

ALBERT, J ;

HAMILTON, AD .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (24) :1761-1763

[9] STUDIES CONCERNING ANTIBIOTIC ACTINONIN .1. CONSTITUTION OF ACTINONIN - NATURAL HYDROXAMIC ACID WITH ANTIBIOTIC ACTIVITY [J].

GORDON, JJ ;

DEVLIN, JP ;

EAST, AJ ;

OLLIS, WD ;

SUTHERLAND, IO ;

WRIGHT, DE ;

NINET, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (09) :819-825

[10] HIGHLY SELECTIVE BINDING OF SIMPLE PEPTIDES BY A C3 MACROTRICYCLIC RECEPTOR [J].

HONG, JI ;

NAMGOONG, SK ;

BERNARDI, A ;

STILL, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5111-5112