Design,synthesis and structure determination of new inherently chiral para-bromoalkoxycalix[4]arenes |
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| Authors: | Oleksandr A Yesypenko Marija A Klyachina Maksym V Dekhtyarenko Vladimir V Pirozhenko Svitlana V Shishkina Vyacheslav I Boyko |
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| Institution: | 1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraineesipenko@ioch.kiev.ua;3. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine;4. Department of Chemistry, Kiev National Taras Shevchenko University, Kiev, Ukraine;5. STC ‘Institute for Single Crystals’, National Academy of Sciences of Ukraine, Kharkiv, Ukraine;6. Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, Kharkiv, Ukraine |
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| Abstract: | The preparative method for the synthesis of inherently chiral para-bromoalkoxycalix4]arenes based on para-bromination, stepwise regioselective debenzoylation and the following alkylation of the readily available 25-propoxy-26,27-dibenzoyloxycalix4]arene with propyl bromide or (R)-N-(1-phenylethyl)bromoacetamide has been developed. Three types of the inherently chiral calix4]arenes in cone or partial cone conformations with asymmetrical (AHHHHBHH, AAHHHBHH, AHBHHCHH) substitution of both upper and lower rims have been obtained in racemic, diastereomerically pure or enantiomerically pure forms. Their structure and the absolute configuration have been determined by NMR and X-ray. |
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| Keywords: | Inherently chiral calix[4]arenes stereoselective synthesis diastereomers enantiomers optical resolution |
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