Design, synthesis and structure determination of new inherently chiral para-bromoalkoxycalix[4]arenes

作者：Yesypenko Oleksandr A^*; Klyachina Marija A; Dekhtyarenko Maksym V; Pirozhenko Vladimir V; Shishkina Svitlana V; Boyko Vyacheslav I; Voitenko Zoia V; Kalchenko Vitaly I

来源：Supramolecular Chemistry, 2017, 29(1): 49-58.

DOI：10.1080/10610278.2016.1167210

• Inherently chiral calix[4]arenes
• stereoselective synthesis
• diastereomers
• enantiomers
• optical resolution

The preparative method for the synthesis of inherently chiral para-bromoalkoxycalix[4]arenes based on para-bromination, stepwise regioselective debenzoylation and the following alkylation of the readily available 25-propoxy-26,27-dibenzoyloxycalix[4]arene with propyl bromide or (R)-N-(1-phenylethyl)bromoacetamide has been developed. Three types of the inherently chiral calix[4] arenes in cone or partial cone conformations with asymmetrical ((HBHH)(AHHH), (HBHH)(AAHH), (HCHH)(AHBH)) 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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• 出版日期2017