Resolution of inherently chiral anti-O,O′-dialkylated calix[4]arenes and determination of their absolute stereochemistries by CD and X-ray methods |
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| Institution: | 1. Department of Basic Sciences, School of Science and Engineering, Ishinomaki Senshu University, 1 Shinmito, Minamisakai, Ishinomaki 986-8580, Japan;2. Department of Environmental Studies, Graduate School of Environmental Studies, Tohoku University, 6-6-07, Aramaki-Aoba, Aoba-ku, Sendai 980-8579, Japan;3. Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki-Aoba, Aoba-ku, Sendai 980-8578, Japan;1. Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland;2. Department of Chemistry, University of Wrocław, F. Joliot-Curie St. 14, 50-383 Wrocław, Poland;3. Faculty of Chemistry, Wrocław University of Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, Poland;1. School of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, PR China;2. Jiangsu Chia Tai Qingjiang Pharmaceutical Co., Ltd, PR China;3. Department of Chemical and Pharmaceutical Engineering of Southeast University Chengxian College, Nanjing 210088, PR China;1. Laboratorium für Organische Chemie, ETH Zürich, Hönggerberg, HCI, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland;2. Laboratoire d''Electrochimie et de Chimie Physique du Corps Solide, Institute de Chimie-UMR 7177, CNRS, Université de Strasbourg, 4, rue Blaise Pascal, CS 90032, 67081 Strasbourg Cedex, France |
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| Abstract: | Inherently chiral anti-O,O′-dibenzyl-p-tert-butylcalix4]arene 1 was resolved as the (S)-2-methoxy-2-(naphthalen-1-yl)propionic ester by flash chromatography. Conversely, the anti-O,O′-dibutyl analogue 2 was resolved as the (Sa)-2′-methoxy-1,1′-binaphthalene-2-carboxylic ester by crystallization combined with flash chromatography. CD analysis of these compounds indicated the absolute stereochemistries to be (Sa)-(+)-1 and (Sa)-(+)-2, respectively, the former of which was confirmed by X-ray crystallographic analysis. |
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