Chemodivergent Spirocyclization of 2‐Sec‐Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis

Chemodivergent Spirocyclization of 2‐Sec‐Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis

Benzylidene imidazolones with ortho‐ secondary aminogroup undergo acid‐promoted chemodivergent spirocyclization. Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]‐hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids p...

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Veröffentlicht in:Advanced synthesis & catalysis 2022-04, Vol.364 (9), p.1587-1595
Hauptverfasser: Ivanov, Dmitrii S., Zaitseva, Elvira R., Smirnov, Alexander Yu, Rustamova, Dina A., Mikhaylov, Andrey A., Sycheva, Maria A., Gluschenko, Darya A., Baleeva, Nadezhda S., Baranov, Mikhail S.
Format: Artikel
Sprache:eng
Schlagworte:
[1,5]-hydride shift
Acids
Heterocyclic compounds
intramolecular hydroamination
Lewis acid
spiroindolines
spirotetrahydroquinolines
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Zusammenfassung:Benzylidene imidazolones with ortho‐ secondary aminogroup undergo acid‐promoted chemodivergent spirocyclization. Strong Lewis acids provide access to spirocyclic tetrahydroquinolines via [1,5]‐hydride shift triggered cyclization despite of the presence of free secondary amino group. Brønsted acids promote unprecedented intramolecular umpolung hydroamination reaction with the formation of spirocyclic indolines. Each of the processes proceeds with exclusive atom‐economy.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202200109