Synthesis of C-Alkylcalix[4] arenes. 4. Design, Synthesis, and Computational Studies of Novel Chiral Amido[4]resorcinarenes

Bruno Botta, Giuliano Delle Monache, Patrizia Salvatore, Francesco Gasparrini, Claudio Villani, Maurizio Botta, Federico Corelli, Andrea Tafi, Eszter Gacs-Baitz, Antonello Santini, Cristopher F. Carvalho, Domenico Misiti

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Abstract

In extending our studies involving BF3·Et2O-catalyzed reaction of cinnamic acid analogues, we have shown that amido derivatives also can afford [4]resorcinarene octamethyl ethers. Subsequently, chiral monomeric amides, derived from the mixed anhydride of cinnamic acid and L- or D-valine, upon treatment with BFa·Et2O, yielded for the first time chiral amido [4]resorcinarenes in enantiomerically pure forms. Four stereoisomers were isolated, and three of them were attributed the flattened-cone, chair, and 1,2-alternate conformations. The major product was assigned a novel chairlike structure, namely flattened partial cone 1. The flattened-cone stereoisomer, which was indicated by molecular modeling studies to be the most stable, became the major product under more drastic experimental conditions. Chromatographic studies on chiral phases revealed that the above tetramers could be used for the enantiodiscrimination of racemic molecules.

Original languageEnglish
Pages (from-to)932-938
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number4
Publication statusPublished - Dec 1 1997

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Botta, B., Monache, G. D., Salvatore, P., Gasparrini, F., Villani, C., Botta, M., Corelli, F., Tafi, A., Gacs-Baitz, E., Santini, A., Carvalho, C. F., & Misiti, D. (1997). Synthesis of C-Alkylcalix[4] arenes. 4. Design, Synthesis, and Computational Studies of Novel Chiral Amido[4]resorcinarenes. Journal of Organic Chemistry, 62(4), 932-938.