Resolution of inherently chiral calix[4]arenes with AABB and CDCD substitution patterns on the upper and lower rims, respectively

被引：35

作者：

Caccamese, S

Bottino, A

Cunsolo, F

Parlato, S

Neri, P

机构：

[1] Univ Salerno, Dipartimento Chim, I-84081 Baronissi, SA, Italy

[2] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy

[3] CNR, Ist Studio Sostanze Nat Interesse Alimentare & Ch, I-95028 Valverde, CT, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(00)00273-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Proximal di-tert-butylcalix[4]arene (5,11-di-tert-butylcalix[4]arene-25,26,27,28-tetrol) 1b, obtained by direct partial removal of tert-butyl groups from p-tert-butylcalix[4]arene, gave high yields of inherently chiral derivatives upon 'symmetry breaking' by syn-distal di-O-alkylation or di-O-acylation in the presence of K2CO3 The chirality of these compounds was proven by the splitting of H-1 NMR signals in the presence of Pirkle's reagent and in some cases by HPLC enantiomeric resolution using chiral stationary phases and corroborated by mirror-image CD spectra. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3103 / 3112

页数：10

共 41 条

[1]

ALLENMARK S, 1991, CHROMATOGRAPHIC ENAN, P51

[2] DISSYMMETRIC CALIX[4]ARENES WITH C4-SYMMETRY AND C2-SYMMETRY - SYNTHESIS, X-RAY STRUCTURES, CONFORMATIONAL FIXATION, AND H-1-NMR SPECTROSCOPIC STUDIES [J].