Preparation of enantiomers of 9-(1-amino-2,2-dimethylpropyl)-9,10-dihydroanthracene. Conformational study and their behaviour as chiral solvating agents

被引:21
作者
Port, A [1 ]
Virgili, A [1 ]
Jaime, C [1 ]
机构
[1] UNIV AUTONOMA BARCELONA,DEPT QUIM,E-08193 BELLATERRA,SPAIN
关键词
D O I
10.1016/0957-4166(96)00146-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Homochiral forms of 9-(1-amino-2,2-dimethylpropyl)-9,10-dihydroanthracene were prepared by hydrolysis of crystallised diastereomeric salts of mandelic acid. The activity as chiral solvating agent was tested in the presence of several alcohols and acids. A boat conformation of the central ring was demonstrated by NMR studies and MM3 calculations. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1295 / 1302
页数:8
相关论文
共 17 条
[1]  
ALLINGER NL, 1989, J AM CHEM SOC, V111, P8522
[2]   Use of 9-anthrylcarbinol derivatives as chiral auxiliaries in asymmetric Diels-Alder reaction [J].
Carriere, A ;
Virgili, A .
TETRAHEDRON-ASYMMETRY, 1996, 7 (01) :227-230
[3]   CONFORMATIONAL STUDIES BY DYNAMIC NMR .48. CONFORMATIONAL PREFERENCES AND STEREOMUTATIONAL PROCESSES OF THE ROTATIONAL ENANTIOMERS OF HINDERED NAPHTHYLIMINES AND IMONIUM SALTS [J].
CASARINI, D ;
LUNAZZI, L ;
MACCIANTELLI, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (08) :1363-1370
[4]   PREPARATION OF HOMOCHIRAL 9-ANTHRYL-TERT-BUTYLCARBINOL - THE CONFIGURATIONAL AND CONFORMATIONAL NMR-STUDY OF ITS CARBAMATE DERIVATIVES [J].
DEMORAGAS, M ;
PORT, A ;
SANCHEZRUIZ, X ;
JAIME, C ;
ROUSSEL, C ;
VIRGILI, A .
TETRAHEDRON-ASYMMETRY, 1995, 6 (06) :1307-1310
[5]   RESTRICTED ROTATION AND NOE TRANSFER - A CONFORMATIONAL STUDY OF SOME SUBSTITUTED (9-ANTHRYL)CARBINOL DERIVATIVES [J].
DERIGGI, I ;
VIRGILI, A ;
DEMORAGAS, M ;
JAIME, C .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) :27-31
[6]   AN INVESTIGATION OF SUBSTITUENT EFFECTS ON THE CONFORMATION OF 9,10-DIHYDROANTHRACENES BY MOLECULAR MECHANICS CALCULATIONS AND X-RAY STRUCTURE-ANALYSIS [J].
DHAR, RK ;
SYGULA, A ;
FRONCZEK, FR ;
RABIDEAU, PW .
TETRAHEDRON, 1992, 48 (43) :9417-9426
[7]   A CHIRAL SOLVATING AGENT FOR DIRECT NMR ASSAY OF THE ENANTIOMERIC PURITY OF CARBOXYLIC-ACIDS [J].
FULWOOD, R ;
PARKER, D .
TETRAHEDRON-ASYMMETRY, 1992, 3 (01) :25-28
[8]   1,2-DIPHENYLETHANE-1,2-DIAMINE - AN EFFECTIVE NMR CHIRAL SOLVATING AGENT FOR CHIRAL CARBOXYLIC-ACIDS [J].
FULWOOD, R ;
PARKER, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (01) :57-64
[9]   ANALYSIS OF CHIRAL CARBOXYLIC-ACIDS BY NMR USING NEW OPTICALLY-ACTIVE AMINES [J].
KUHN, M ;
BUDDRUS, J .
TETRAHEDRON-ASYMMETRY, 1993, 4 (02) :207-210
[10]  
MARTYNOFF M, 1963, B SOC CHIM FR, V30, P346