Asymmetric Synthesis of Inherently Chiral Tetraoxacalix[2]arene[2]pyridines via S<sub>N</sub>Ar‐Based Cross‐Cyclotetramerization
Potassium phosphate-promoted cross-cyclotetramerization of 2,6-dichloro-3-nitropyridine 1 with resorcinol derivatives 2 gave rise to thermodynamically favored 1,3-alternate tetraoxacalix[2]arene[2]pyridines and kinetically controlled 1,2-alternate isomers. The kinetic product could convert into its 1,3-alternate conformational isomer by a macrocycle to macrocycle conversion pathway. Enantiomerically enriched C<sub>2</sub>-symmetric inherently chiral tetraoxacalix[2]arene[2]pyridines were synthesized via a Cinchonine-derived chiral phase-transfer catalyst (PTC). This synthesis involved the cross-cyclotetramerization of 1 with 2, featuring a key enantioselective intramolecular aromatic nucleophilic substitution (S<sub>N</sub>Ar) step.
Authors
- Shuo Tong (ORCID: https://orcid.org/0000-0002-7982-2546)
- R. R. Ibragimova (ORCID: https://orcid.org/0000-0002-6406-9643)
- Jieping Zhu (ORCID: https://orcid.org/0000-0002-8390-6689)
- Mei‐Xiang Wang (ORCID: https://orcid.org/0000-0001-7112-0657)
- Qiu-Lin Lu
Institutions
- École Polytechnique Fédérale de Lausanne (CH)
- Tsinghua University (CN)
Publication Details
- Journal
- Chemistry - An Asian Journal
- Published
- 2025-01-29
- DOI
- https://doi.org/10.1002/asia.202401621
- Citations
- 4
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- National Natural Science Foundation of China
- Tsinghua University