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Combining Imine Condensation Chemistry with [3,3] Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures.
- Source :
- Angewandte Chemie International Edition; 7/24/2023, Vol. 62 Issue 30, p1-5, 5p
- Publication Year :
- 2023
-
Abstract
- Dynamic covalent chemistry (DCC) has, in recent years, provided valuable tools to synthesize molecular architectures of increasing complexity. We have also taken advantage of imine DCC chemistry to prepare TPMA‐based supramolecular cages for molecular recognition applications. However, the versatility of this approach has as a major drawback the intrinsic hydrolytic lability of imines, which hampers some applications. We present herein a synthetic strategy that combines the advantages of a thermodynamic‐driven formation of a supramolecular structure using imine chemistry, together with the possibility to synthetize chiral hydrolytically stable structures through a [3,3]‐sigmatropic rearrangement. A preliminary mechanistic analysis of this one‐pot synthesis and the scope of the reaction are also discussed. [ABSTRACT FROM AUTHOR]
- Subjects :
- SIGMATROPIC rearrangements
CONDENSATION
IMINES
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 62
- Issue :
- 30
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 165045524
- Full Text :
- https://doi.org/10.1002/anie.202304490