Diastereoselective Synthesis of Tetrahydroquinolines Bearing Oxindole Scaffolds via Annulation of in Situ Generated p‐Quinone Methides. Issue 13 (11th May 2020)

• Record Type: Journal Article
• Authors: Wang, Junwei; Zhao, Lei; Zhao, Lin; Pan, Xiang; Lv, Cheng; Zhi, Ying; Wang, Ai; Zhao, Kun; Hu, Lihong
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 13(2020)
• Page Start: 2755
• Page End: 2759
• Publication Date: 2020-05-11
• Subjects: [4+2] annulation reaction -- p-quinone methides -- isatin-derived enoates -- cascade reaction -- 4-phenyl-tetrahydroquinolines; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000436
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A diastereoselective [4+2] annulation reaction between in situ generated p ‐quinone methides and isatin‐derived enoates has been developed. In the presence of manganese dioxide as an oxidant, a variety of tosylaminophenyl‐substituted p ‐quinone methide intermediates can be readily generated in an in situ fashion. Without pre‐preparation of p ‐QMs, this unprecedented cascade reaction proceeds efficiently under mild conditions, providing a straightforward route to synthesize 4‐phenyl‐substituted tetrahydroquinolines bearing 3, 3'‐spirooxindole scaffolds in good yields. Abstract :