Efficient synthesis of hexahydroindenopyridines and their potential as melatoninergic ligands

Párraga, Javier; Moreno, Laura; Dı́az, A. Navas; Aouad, Noureddine El; Galán, Abraham; Sanz, María-Jesús; Caignard, Daniel‐Henri; Figadère, Bruno; Cabedo, Nuria; Cortés, Diego

doi:10.1016/j.ejmech.2014.09.038

Cited by 6 publications

(1 citation statement)

References 24 publications

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“…Chiral 2-alkyl piperidine is a ubiquitous motif found in a wide range of medicinally important compounds including many naturally occurring alkaloids (Figure ). , 2-Alkyl piperidine-containing molecules have exhibited a broad spectrum of interesting biological activities such as potential analgetics, antiamnestic agents, and for the treatment of neurological diseases and psychiatric disorders…”

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confidence: 99%

Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts

Mangunuru

Wei

et al. 2016

Org. Lett.

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An Ir-catalyzed enantioselective hydrogenation of 2-alkyl-pyridines has been developed using ligand MeO-BoQPhos. High levels of enantioselectivities up to 93:7 er were obtained. The resulting enantioenriched piperidines can be readily converted into biologically interesting molecules such as the fused tricyclic structures 5, 6, and 7 in 99:1 er, providing a novel, concise synthetic route to this family of chiral piperidine-containing compounds.

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confidence: 99%

Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts

Mangunuru

Wei

et al. 2016

Org. Lett.

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Cinchonamine Squaramide Catalyzed Asymmetric aza‐Michael Reaction: Dihydroisoquinolines and Tetrahydropyridines

2018

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The first example of ac hiral cinchona-squaramide catalyzede nantioselective intramolecular aza-Michael addition for the synthesis of dihydroisoquinolines and tetrahydropyridines has been developed. In general, good yields and excellent enantioselctivities were observed. Broad classes of Michael acceptors,s uch as enones,e sters,t hioesters,a nd Weinreb amides,w ere successful substrates.T he possibility of recycling the catalysts has also been demonstrated. An oxidation of combined enamine and keto functionalities on chiral dihydroisoquinolines leads to asingle diastereomer of an architecturally unprecedented tetracyclic core without loss in enantioselectivity. Figure 1. Representativebioactive compounds.

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Cinchonamine Squaramide Catalyzed Asymmetric aza‐Michael Reaction: Dihydroisoquinolines and Tetrahydropyridines

2018

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The first example of a chiral cinchona-squaramide catalyzed enantioselective intramolecular aza-Michael addition for the synthesis of dihydroisoquinolines and tetrahydropyridines has been developed. In general, good yields and excellent enantioselctivities were observed. Broad classes of Michael acceptors, such as enones, esters, thioesters, and Weinreb amides, were successful substrates. The possibility of recycling the catalysts has also been demonstrated. An oxidation of combined enamine and keto functionalities on chiral dihydroisoquinolines leads to a single diastereomer of an architecturally unprecedented tetracyclic core without loss in enantioselectivity.

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Efficient synthesis of hexahydroindenopyridines and their potential as melatoninergic ligands

Cited by 6 publications

References 24 publications

Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts

Synthesis of Enantioenriched 2-Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts

Cinchonamine Squaramide Catalyzed Asymmetric aza‐Michael Reaction: Dihydroisoquinolines and Tetrahydropyridines

Cinchonamine Squaramide Catalyzed Asymmetric aza‐Michael Reaction: Dihydroisoquinolines and Tetrahydropyridines

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