4.8 Article

Calix[6]arene Threading with Weakly Interacting Tertiary Ammonium Axles: Generation of Chiral Pseudorotaxane Architectures

Journal

ORGANIC LETTERS
Volume 17, Issue 4, Pages 1006-1009

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b00115

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Funding

  1. Italian MIUR [PRIN 20109Z2XRJ_006]
  2. Centro di Tecnologie Integrate per la Salute, Universita di Salerno [PONa3_00138]

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The TFPB superweak anion effectively induces the threading of a scarcely preorganized calix[6]arene (1) with weakly interacting tertiary ammonium axles (2(+)3(+)). The pseudorotaxanes (4(+)5(+)) thus formed show an unexpected chirality due to an unprecedented formation of a threading-induced stereogenic ammonium center.

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