Access to chiral calix[4]arenes can unlock novel supramolecular architectures for enantioselective catalysis and molecular recognition. However, accessibility to these structures has been significantly hindered so far. We report herein the synthesis and characterization of di- and trifunctionalized cone-calix[4]arenes featuring a lactone moiety spanning the distal positions at the upper rim. The lactones force the whole skeleton to assume pinched- cone conformations. The ring-closure is favored by the high conformational flexibility of the calixarene scaffold. The new lactones are remarkably stable in the solid state, while a quick hydrolysis to restore the parent carboxylic acids occurs in solution under acidic/basic conditions.

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Slow aminolyses of lactones 2–3 yield inherently chiral products featuring three different functionalities at the upper rim, at room temperature. The subsequent ring-closing/opening methodology presented here highlights the versatility of these lactones as powerful synthons for the preparation of a variety of threefold upper rim functionalized, inherently chiral calix[4]arenes fixed in the cone structure. • For reproduction of material from NJC: Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry. • For reproduction of material from PCCP: Reproduced from Ref. XX with permission from the PCCP Owner Societies. • For reproduction of material from PPS: Reproduced from Ref.

XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry. • For reproduction of material from all other RSC journals and books: Reproduced from Ref. XX with permission from The Royal Society of Chemistry. If the material has been adapted instead of reproduced from the original RSC publication 'Reproduced from' can be substituted with 'Adapted from'. In all cases the Ref. XX is the XXth reference in the list of references. If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc.

Contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material. Reproduced material should be attributed as follows.

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