Planar Chiral [2.2]Paracyclophane-Based Bisoxazoline Ligands and Their Applications in Cu-Mediated N–H Insertion Reaction

Daniel M Knoll,Stefan Bräse,Martin Nieger,Yuling Hu,Zahid Hassan

doi:10.3390/molecules24224122

Daniel M Knoll, Stefan Bräse + Show 3 more

Open Access

https://doi.org/10.3390/molecules24224122

Copy DOI

Abstract

New catalysts for important C–N bond formation are highly sought after. In this work, we demonstrate the synthesis and viability of a new class of planar chiral [2.2]paracyclophane-based bisoxazoline (BOX) ligands for the copper-catalyzed N–H insertion of α-diazocarbonyls into anilines. The reaction features a wide substrate scope and moderate to excellent yields, and delivers the valuable products at ambient conditions.

Highlights

The copper-catalyzed N–H insertion of carbenoids such as prepared α-diazocarbonyls isThe copper-catalyzed N–H insertion of carbenoids such as prepared α-diazocarbonyls is a powerful method for bioactivemolecules moleculesand and pharmaceutical a powerful method forthe thepreparation preparationof ofhighly highly valuable valuable bioactive pharmaceutical products [1]
We showed the synthesis and catalytic application of three different PCPBOX ligands
The N–H insertion into saturated anilines was demonstrated to afford moderate to excellent yields with a wide substrate scope

Summary

Introduction

The copper-catalyzed N–H insertion of carbenoids such as prepared α-diazocarbonyls is. The copper-catalyzed N–H insertion of carbenoids such as prepared α-diazocarbonyls is a powerful method for bioactivemolecules moleculesand and pharmaceutical a powerful method forthe thepreparation preparationof ofhighly highly valuable valuable bioactive pharmaceutical products [1]. InInthe enantioselectivechelating chelatingligands ligands based bis(oxazoline) products[1]. Thepast pastdecade, decade, various various enantioselective based onon thethe bis(oxazoline) motifs have been established for this transformation (Figure 1) [2,3,4,5,6,7,8]. Motifs have been established for this transformation Reference source not found.) [2,3,4,5,6,7,8].

Methods

Results

Conclusion