Photoinduced Copper-Catalyzed Regio- and Diastereoselective Multicomponent [3 + 2 + 1] Radical Cyclization To Access Tetrahydropyridines DOI
Sijia Li,

Jianye Li,

He Zhang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 12, 2025

The use of simple raw materials to construct complex piperidine scaffolds via multicomponent reactions is highly desirable from the perspectives atom and step-economy. In this Letter, we present a photoinduced copper-catalyzed three- or four-component [3 + 2 1] radical cyclization, utilizing inexpensive readily available feedstock amines, alkynes, aldehydes, synthesize multisubstituted bicyclic spirocyclic tetrahydropyridines. This method notable for its mild conditions, atom-economic approach, excellent regio- diastereoselectivity, simultaneous activation two α-amino C(sp3)-H bonds, resulting in formation three C-C bonds one C-N bond single step. Mechanistic studies suggest that α-aminoalkyl key intermediate reaction, which undergoes sequential addition, 1,5-HAT, 6-exo-trig-type cyclization.

Language: Английский

Photoinduced Copper-Catalyzed Regio- and Diastereoselective Multicomponent [3 + 2 + 1] Radical Cyclization To Access Tetrahydropyridines DOI
Sijia Li,

Jianye Li,

He Zhang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 12, 2025

The use of simple raw materials to construct complex piperidine scaffolds via multicomponent reactions is highly desirable from the perspectives atom and step-economy. In this Letter, we present a photoinduced copper-catalyzed three- or four-component [3 + 2 1] radical cyclization, utilizing inexpensive readily available feedstock amines, alkynes, aldehydes, synthesize multisubstituted bicyclic spirocyclic tetrahydropyridines. This method notable for its mild conditions, atom-economic approach, excellent regio- diastereoselectivity, simultaneous activation two α-amino C(sp3)-H bonds, resulting in formation three C-C bonds one C-N bond single step. Mechanistic studies suggest that α-aminoalkyl key intermediate reaction, which undergoes sequential addition, 1,5-HAT, 6-exo-trig-type cyclization.

Language: Английский

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