Chemodivergent Spirocyclization of 2‐Sec‐Aminobenzilidene Imidazolones: Lewis Versus Brønsted Acids Catalysis. Issue 9 (8th April 2022)

• Record Type: Journal Article
• Authors: 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.
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 9(2022)
• Page Start: 1587
• Page End: 1595
• Publication Date: 2022-04-08
• Subjects: [1, 5]-hydride shift -- intramolecular hydroamination -- spiroindolines -- spirotetrahydroquinolines; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200109
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :