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

Autor: Karpus A; 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.; Taras Shevchenko National University of Kyiv , 64/13 Volodymyrska Street, 01033 Kyiv, Ukraine., Yesypenko O; Institute of Organic Chemistry NAS of Ukraine , Murmanska Street 5, 02660 Kyiv, Ukraine., Boiko V; Institute of Organic Chemistry NAS of Ukraine , Murmanska Street 5, 02660 Kyiv, Ukraine., Daran JC; 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., Voitenko Z; Taras Shevchenko National University of Kyiv , 64/13 Volodymyrska Street, 01033 Kyiv, Ukraine., Kalchenko V; Institute of Organic Chemistry NAS of Ukraine , Murmanska Street 5, 02660 Kyiv, Ukraine., Manoury E; 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.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2018 Feb 02; Vol. 83 (3), pp. 1146-1153. Date of Electronic Publication: 2018 Jan 24.
DOI: 10.1021/acs.joc.7b02312
Abstrakt: 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.
Databáze: MEDLINE
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