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- Title
Combining Imine Condensation Chemistry with [3,3] Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures.
- Authors
Begato, Federico; Penasa, Roberto; Wurst, Klaus; Licini, Giulia; Zonta, Cristiano
- 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.
- Subjects
SIGMATROPIC rearrangements; CONDENSATION; IMINES
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 30, p1
- ISSN
0044-8249
- Publication type
Academic Journal
- DOI
10.1002/ange.202304490