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

被引:34
作者
Caccamese, S
Notti, A
Pappalardo, S
Parisi, MF
Principato, G
机构
[1] Univ Catania, Dipartimento Sci Chim, I-95125 Catania, Italy
[2] Univ Messina, Dipartimento Chim Organ & Biol, I-98166 Messina, Italy
关键词
asymmetry; calixarenes; crown ethers; enantioselective resolution;
D O I
10.1016/S0040-4020(99)00195-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of alpha-picolyloxy-p-tert-butylcalix[5]arene with tri- to pentaethylene glycol ditosylates and K2CO3 regioselectively affords racemic (1,2)-bridged crown ether derivatives in the cone conformation. Their structure is firmly established by NMR spectroscopy and by comparison with appropriate (1,3)-bridged crown-6 regioisomers, synthesized by unequivocal sequences. The enantiomeric resolution of racemates has been achieved by direct HPLC separation, using enantioselective stationary phases. The enantiomers of the (1,2)-bridged crown-5 derivative exhibit one of the largest separation factors (alpha) so far reported for inherently chiral calixarenes. (C) 1999 Elsevier Science Ltd, All rights reserved.
引用
收藏
页码:5505 / 5514
页数:10
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