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Selective Macrocycle Formation in Cavitands

Ji-Min Yang, Yang Yu and Julius Rebek Jr.

*Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States, Email: jrebekscripps.edu

J.-M. Yang, Y. Yu, J. Rebek Jr., J. Am. Chem. Soc., 2021, 143, 2190-2193.

DOI: 10.1021/jacs.0c12302


Abstract

The unfavorable entropy of macrocyclic closure allows undesired intermolecular reactions to compete. The use of cavitands for the selective intramolecular aldol/dehydration reaction of long-chain α,ω-dialdehydes in aqueous solution favors macrocyclization reactions over intermolecular reactions due to hydrophobic forces driving the dialdehydes into the cavitands in folded conformations.

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Key Words

aldol condensation


ID: J48-Y2021