Journal
ORGANIC LETTERS
Volume 17, Issue 15, Pages 3650-3653Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01455
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- Semyaku from the Ministry of Education, Culture, Sports, Science and Technology of Japan
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A calix[3]aramide has been synthesized bearing three triphenylphosphinic amide moieties, which formed intramolecular cyclic hydrogen bonds that suppressed its cone/partial cone inversion. The intramolecular cyclic hydrogen bonds were disrupted by DMSO, and the insertion of H2O into the hydrogen bonds triggered the spontaneous resolution of the calix[3]aramide. Within a chiral environment, such as that afforded by the presence of optically active 2-butanol, the calix[3]aramide underwent a symmetry breaking crystallization process.
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