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A general method for obtaining calix[4]arene derivatives in the 1,2-alternate conformation

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JournalTetrahedron
DateAccepted/In press - 9 Aug 2016
DateE-pub ahead of print - 13 Aug 2016
DatePublished (current) - 13 Oct 2016
Issue number41
Volume72
Number of pages8
Pages (from-to)6348-6355
Early online date13/08/16
Original languageEnglish

Abstract

The 1,2-alternate conformation, so far the least accessible atropisomer of calix[4]arene, is now easily available on a gram scale. The entire synthetic sequence consists of only two steps—(a) proximal dialkylation (R1-I, NaH/DMF), and (b) another subsequent dialkylation (R2-I, Me3SiOK/THF). The selection of appropriate base/solvent combinations in both stages was the key prerequisite for the successful preparation of the 1,2-alternate conformers, which are available without the use of any protecting groups.

    Research areas

  • 1,2-Alternate, Alkylation, Calixarene, Conformation, Conformational mobility, Partial cone

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