Université Toulouse III-Paul Sabatier , 118 route de Narbonne, 31062 Toulouse Cedex 9, France.
Laboratoire de Chimie de Coordination du CNRS , 205 route de Narbonne, 31077 Toulouse Cedex 4, France.
J Org Chem. 2018 Feb 2;83(3):1146-1153. doi: 10.1021/acs.joc.7b02312. Epub 2018 Jan 24.
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 Brönsted 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.
开发了一种从易得的先前合成的（cS）-对映体杯[4]乙酸 1 或其甲酯 2 出发，经四步反应制备对映体纯的固有手性杯[4]膦酸（cR，pR）-7 的简便方法。首次在手性杯[4]芳烃 Brønsted 酸的有机催化作用下，对亚胺与 Danishefsky 二烯的氮杂-Diels-Alder 反应以及苯甲酸的环氧化合物开环反应进行了测试。在这些反应中，杯[4]膦酸（cR，pR）-7 显示出良好的催化活性，但对映选择性低。
