Combining Imine Condensation Chemistry with [3,3] Diaza‐Cope Rearrangement for One‐Step Formation of Hydrolytically Stable Chiral Architectures

Author:

Begato Federico1ORCID,Penasa Roberto1ORCID,Wurst Klaus2ORCID,Licini Giulia1ORCID,Zonta Cristiano1ORCID

Affiliation:

1. Department of Chemical Sciences University of Padova Via Marzolo 1 35131 Padova Italy

2. Department of General Inorganic and Theoretical Chemistry University of Innsbruck 6020 Innsbruck Austria

Abstract

AbstractDynamic 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.

Funder

Fondazione Cassa di Risparmio di Padova e Rovigo

Publisher

Wiley

Subject

General Medicine

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