Synthesis of a chiral macrocyclic dibenzodicyclohexanotetraamide-containing stationary phase for liquid chromatography

被引：8

作者：

Hu, KJ ^{[1
]}

Bradshaw, JS ^{[1
]}

Dalley, NK ^{[1
]}

Krakowiak, KE ^{[1
]}

Wu, NJ ^{[1
]}

Lee, ML ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1999年 / 36卷 / 02期

关键词：

D O I：

10.1002/jhet.5570360209

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allyloxy-substituted macrocyclic dibenzodicyclohexanotetraamide 2 was prepared by the following sequence. MonoBoc-protected chiral 1,2-cyclohexanediamine (3) was treated with isophthaloyl chloride followed by removal of the Boc group to form bisisophthalamide 5. Compound 5 was then treated with allyloxyphthaloyl chloride to form the macrocyclic tetraamide 2 in a 56% yield. Chiral selector 2 was converted to its ethoxydimethylsilane derivative and heated in a suspension of silica gel and toluene to form the chiral macrocycle-containing silica gel phase 1. This phase separated the enantiomers of (+/-)-alpha-methylbenzylamine and (+/-)-DL-alpha-aminobutyric acid methyl ester in a liquid chromatograph.

引用

页码：381 / 387

页数：7

共 30 条

[1]

Ahuja S., 1997, Chiral Separations Applications and technology, V1st

[2] CHIRAL ALPHA-SUBSTITUTED ALPHA-ARYLOXY ACETIC-ACIDS - SYNTHESIS, ABSOLUTE-CONFIGURATION, CHEMICAL RESOLUTION, AND DIRECT SEPARATION BY HPLC [J].

BETTONI, G ;

FERORELLI, S ;

LOIODICE, F ;

TANGARI, N ;

TORTORELLA, V ;

GASPARRINI, F ;

MISITI, D ;

VILLANI, C .

CHIRALITY, 1992, 4 (03) :193-203

[3] STABLE SILICA GEL-BOUND CROWN ETHERS - SELECTIVE SEPARATION OF METAL-IONS AND A POTENTIAL FOR SEPARATIONS OF AMINE ENANTIOMERS [J].

BRADSHAW, JS ;

IZATT, RM ;

CHRISTENSEN, JJ ;

KRAKOWIAK, KE ;

TARBET, BJ ;

BRUENING, RL ;

LIFSON, S .

JOURNAL OF INCLUSION PHENOMENA, 1989, 7 (02) :127-136

[4] PREPARATION OF SILICA GEL-BOUND MACROCYCLES AND THEIR CATION-BINDING PROPERTIES [J].

BRADSHAW, JS ;

BRUENING, RL ;

KRAKOWIAK, KE ;

TARBET, BJ ;

BRUENING, ML ;

IZATT, RM ;

CHRISTENSEN, JJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) :812-814

[5] SYNTHESIS OF (ALLYLOXY)METHYL-SUBSTITUTED DIAZA-18-CROWN-6 COMPOUNDS FOR ATTACHMENT TO SILICA-GEL [J].

BRADSHAW, JS ;

KRAKOWIAK, KE ;

BRUENING, RL ;

TARBET, BJ ;

SAVAGE, PB ;

IZATT, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3190-3195

[6] A CONVENIENT AND NOVEL ROUTE TO BIS(ETA-ALKYNE)PLATINUM(0) AND OTHER PLATINUM(0) COMPLEXES FROM SPEIER HYDROSILYLATION CATALYST H2[PTCL6].XH2O - X-RAY STRUCTURE OF [PT((ETA-CH2=CHSIME2)2O)(P-TERT-BU3)] [J].

CHANDRA, G ;

LO, PY ;

HITCHCOCK, PB ;

LAPPERT, MF .

ORGANOMETALLICS, 1987, 6 (01) :191-192

[7] NEW HPLC-CHIRAL STATIONARY PHASES FOR ENANTIOMERIC RESOLUTION OF SULFOXIDES AND SELENOXIDES [J].

GARGARO, G ;

GASPARRINI, F ;

MISITI, D ;

PALMIERI, G ;

PIERINI, M ;

VILLANI, C .

CHROMATOGRAPHIA, 1987, 24 :505-509

[8] CHROMATOGRAPHIC OPTICAL RESOLUTION ON TRANS-1,2-DIAMINOCYCLOHEXANE DERIVATIVES - THEORY AND APPLICATIONS [J].

GASPARRINI, F ;

MISITI, D ;

VILLANI, C .

CHIRALITY, 1992, 4 (07) :447-458

[9] CHROMATOGRAPHIC RESOLUTION OF 1,2-AMINO ALCOHOLS ON A CHIRAL STATIONARY PHASE CONTAINING N,N'-(3,5-DINITROBENZOYL)-TRANS-1,2-DIAMINOCYCLOHEXANE - THEORETICAL AND PRACTICAL ASPECTS [J].

GASPARRINI, F ;

MISITI, D ;

VILLANI, C ;

LATORRE, F .

JOURNAL OF CHROMATOGRAPHY, 1991, 539 (01) :25-36

[10]

GREENE TW, 1991, PROTECTIVE GROUPS OR, P328

← 1 2 3 →