Asymmetric Assisted Tandem Catalysis: Hydroamination followed by Asymmetric Friedel–Crafts Reaction from a Single Chiral N, N, N′, N′‐Tetradentate Pyridylmethylamine‐Based Ligand. Issue 15 (1st July 2016)

• Record Type: Journal Article
• Authors: Aillerie, Alexandre; Rodriguez‐Ruiz, Violeta; Carlino, Romain; Bourdreux, Flavien; Guillot, Régis; Bezzenine‐Lafollée, Sophie; Gil, Richard; Prim, Damien; Hannedouche, Jérôme
• Is Part Of: ChemCatChem. Volume 8:Issue 15(2016)
• Page Start: 2455
• Page End: 2460
• Publication Date: 2016-07-01
• Subjects: asymmetric catalysis -- hydroamination -- N ligands -- organocatalysis -- tandem catalysis; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201600604
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: With the rising interest in asymmetric catalysis promoted by earth‐abundant elements, a chiral ligand will undoubtedly be the most valuable unit of the catalyst. The first proof of concept of the use of a multitask chiral ligand in an asymmetric assisted tandem catalysis protocol that successively combines metallo‐ and organocatalytic processes is reported herein. In this protocol, the chiral ligand of the newly designed rare‐earth catalyst of the first reaction is converted into a novel chiral organocatalyst for the second transformation by the simple addition of HCl. The observation of some enantioinduction in the tandem sequence—alkyne hydroamination followed by enantioselective Friedel–Crafts alkylation—confirms the relay of the chiral N, N, N′, N ′‐tetradentate ligand and the importance of its pyridylmethylamine scaffold. Abstract : Relay race : The first example of an asymmetric assisted tandem catalysis protocol that combines a metallocatalyzed alkyne hydroamination reaction with an asymmetric organocatalyzed Friedel–Crafts reaction is reported. The chiral ligand of the metallocatalyst is converted into a chiral organocatalyst by simple HCl addition. Some enantioinduction confirms the relay of the chiral information between the two catalysts.