Facile synthesis and optical resolution of inherently chiral fluorescent calix[4]crowns: enantioselective recognition towards chiral leucinol

被引：73

作者：

Luo, J ^{[1
]}

Zheng, QY ^{[1
]}

Chen, CF ^{[1
]}

Huang, ZT ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Biol Chem Lab, Beijing 100080, Peoples R China

来源：

TETRAHEDRON | 2005年 / 61卷 / 35期

基金：

中国国家自然科学基金;

关键词：

calix[4]crown; inherently chiral; synthesis; optical resolution; enantioselective recognition;

D O I：

10.1016/j.tet.2005.06.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of tri-O-alkylated inherently chiral fluorescent calix[4]crowns in the cone conformations and a series of tetra-O-alkylated inherently chiral fluorescent calix[4]crowns in the partial cone conformations have been synthesized. By condensing with chiral auxiliary (S)-BINOL, the resulting diastereomers could be separated via preparative TLC. We found that the size of the crown moiety effected the separation of the diastereomers. Further, removal of the BINOL unit by hydrolysis furnished pairs of enantiomers with optical purity. Moreover, we found that a tetra-O-alkylated inherently chiral fluorescent calix[4]crown-6 in the partial cone conformation 6c showed considerable enantioselective recognition capability towards chiral leucinol. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8517 / 8528

页数：12

共 30 条

[1] Synthesis of 1,2-bridged calix[4]arene-biscrowns in the 1,2-alternate conformation [J].

Arduini, A ;

Domiano, L ;

Pochini, A ;

Secchi, A ;

Ungaro, R ;

Ugozzoli, F ;

Struck, O ;

Verboom, W ;

Reinhoudt, DN .

TETRAHEDRON, 1997, 53 (10) :3767-3776

[2] Synthesis, optical resolution and complexation properties of inherently chiral monoalkylated p-tert-butyl-(1,2)-calix[4]crown ethers [J].

ArnaudNeu, F ;

Caccamese, S ;

Fuangswasdi, S ;

Pappalardo, S ;

Parisi, MF ;

Petringa, A ;

Principato, G .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8041-8048

[3] INHERENTLY CHIRAL CALIXARENES [J].

BOHMER, V ;

KRAFT, D ;

TABATABAI, M .

JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1994, 19 (1-4) :17-39

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

Caccamese, S ;

Bottino, A ;

Cunsolo, F ;

Parlato, S ;

Neri, P .

TETRAHEDRON-ASYMMETRY, 2000, 11 (15) :3103-3112

[5] Inherently chiral α-picolyloxy-p-tert-butylcalix[5]arene crown ethers:: Synthesis, structure proof, and enantioselective HPLC resolution [J].

Caccamese, S ;

Notti, A ;

Pappalardo, S ;

Parisi, MF ;

Principato, G .

TETRAHEDRON, 1999, 55 (17) :5505-5514

[6] Preparation of both antipodes of enantiopure inherently chiral calix[4]crowns [J].

Cao, YD ;

Luo, J ;

Zheng, QY ;

Chen, CF ;

Wang, MX ;

Huang, ZT .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) :206-208

[7]

Czarnik A. W., 1992, ACS S SERIES, V538

[8] Diphosphines based on an inherently chiral calix[4]arene scaffold: synthesis and use in enantioselective catalysis [J].

Dieleman, C ;

Steyer, S ;

Jeunesse, C ;

Matt, D .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (17) :2508-2517

[9] SYNTHETIC STRATEGIES TO INHERENTLY CHIRAL CALIX[4]ARENES WITH MIXED LIGATING FUNCTIONALITIES AT THE LOWER RIM [J].

FERGUSON, G ;

GALLAGHER, JF ;

GIUNTA, L ;

NERI, P ;

PAPPALARDO, S ;

PARISI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :42-53

[10] Acid-promoted rearrangement of carbonate functionality anchored to the lower rim of a calix[4]arene skeleton: A new class of chiral calix[4]arene and its chiroptical properties [J].

Hesek, D ;

Inoue, Y ;

Drew, MGB ;

Beer, PD ;

Hembury, GA ;

Ishida, H ;

Aoki, F .

ORGANIC LETTERS, 2000, 2 (15) :2237-2240

← 1 2 3 →