Diastereoselective formation of methylene-bridged glycoluril dimers

被引：47

作者：

Witt, D

Lagona, J

Damkaci, F

Fettinger, JC

Isaacs, L ^{[1
]}

机构：

[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA

[2] Gdansk Tech Univ, Fac Chem, PL-80952 Gdansk, Poland

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 06期

关键词：

D O I：

10.1021/ol991382k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The acid-catalyzed formation of methylene-bridged glycoluril dimers yields the C-2v-diastereomer selectively. Product resubmission experiments establish that the selectivity is the result of thermodynamic control. A modified synthetic route is presented that allows for the preparation of unsymmetrically substituted dimers, We present the X-ray crystal structures of both diastereomers, This class of compounds is useful for studies of self-assembly in aqueous solution.

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页码：755 / 758

页数：4

相关论文

共 38 条

[1] DIENOPHILIC REACTIONS OF 3-[(TRIMETHYLSILYL)OXY]-3-BUTEN-2-ONE [J].

ARDECKY, RJ ;

KERDESKY, FAJ ;

CAVA, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (07) :1483-1485

[2]

Behrend R, 1905, LIEBIGS ANN CHEM, V339, P1

[3]

Boileau J., 1985, Propell. Explos. Pyrot., V10, P118, DOI [10.1002/prep.19850100407, DOI 10.1002/PREP.19850100407]

[4] CONTROL OF SELF-ASSEMBLY AND REVERSIBLE ENCAPSULATION OF XENON IN A SELF-ASSEMBLING DIMER BY ACID-BASE CHEMISTRY [J].

BRANDA, N ;

GROTZFELD, RM ;

VALDES, C ;

REBEK, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (01) :85-88

[5] STABILIZATION OF DYES AGAINST HYDROLYTIC DECOMPOSITION BY THE FORMATION OF INCLUSION-COMPOUNDS [J].

BUSCHMANN, HJ ;

SCHOLLMEYER, E .

JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1992, 14 (02) :91-99

[6]

BUSCHMANN HJ, 1996, Patent No. 19603377

[7] Self-assembling capsules [J].

Conn, MM ;

Rebek, J .

CHEMICAL REVIEWS, 1997, 97 (05) :1647-1668

[8] SYNTHESIS OF A FULLERENE DERIVATIVE OF BENZO[18]CROWN-6 BY DIELS-ALDER REACTION - COMPLEXATION ABILITY, AMPHIPHILIC PROPERTIES, AND X-RAY CRYSTAL-STRUCTURE OF A DIMETHOXY-1,9-(METHANO[1,2]BENZENOMETHANO)FULLERENE[60]BENZENE CLATHRATE [J].

DIEDERICH, F ;

JONAS, U ;

GRAMLICH, V ;

HERRMANN, A ;

RINGSDORF, H ;

THILGEN, C .

HELVETICA CHIMICA ACTA, 1993, 76 (07) :2445-2453

[9] COMPLEXATION OF NEUTRAL MOLECULES BY CYCLOPHANE HOSTS [J].

DIEDERICH, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (03) :362-386

[10] DECAMETHYLCUCURBIT[5]URIL [J].

FLINN, A ;

HOUGH, GC ;

STODDART, JF ;

WILLIAMS, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (11) :1475-1477

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