Synthesis of an Enantiomerically Pure Inherently Chiral Calix[4]Arene Phosphonic Acid and Its Evaluation as an Organocatalyst

被引：17

作者：

Karpus, Andrii ^{[1
,2
,3
]}

Yesypenko, Oleksandr ^{[4
]}

Boiko, Vyacheslav ^{[4
]}

Daran, Jean-Claude ^{[1
,2
]}

Voitenko, Zoia ^{[3
]}

Kalchenko, Vitaly ^{[4
]}

Manoury, Eric ^{[1
,2
]}

机构：

[1] Univ Toulouse III Paul Sabatier, 118 Route Narbonne, F-31062 Toulouse 9, France

[2] CNRS, Lab Chim Coordinat, 205 Route Narbonne, F-31077 Toulouse 4, France

[3] Taras Shevchenko Natl Univ Kyiv, 64-13 Volodymyrska St, UA-01033 Kiev, Ukraine

[4] Inst Organ Chem NAS Ukraine, Murmanska St 5, UA-02660 Kiev, Ukraine

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 03期

关键词：

HYDROGEN-BOND PATTERNS; DIELS-ALDER REACTION; BRONSTED ACIDS; CALIXARENES; RECOGNITION; RESOLUTION; CONFIGURATION; MACROCYCLES; CATALYSTS; EPOXIDES;

D O I：

10.1021/acs.joc.7b02312

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile method for the preparation of enantiomerically pure inherently chiral calix[4]arene phosphonic acid (cR,pR)-7 in four steps starting from the readily available and previously synthesized (cS)-enantiomer of calix[4]arene acetic acid 1 or its methyl ester 2 was developed. The first tests of this unique calixarene Bronsted acid with inherent chirality in organocatalysis of the aza-Diels-Alder reaction of imines with Danishefsky's diene and epoxide ring opening by benzoic acid were performed. The calixarene phosphonic acid (cR,pR)-7 shows good catalytic activities but with low enantioselectivities in these reactions.

引用

页码：1146 / 1153

页数：8

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