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Allylic Acetals as Acrolein Oxonium Precursors in Tandem C-H Allylation and [3+2] Dipolar Cycloaddition.

Lee, Heeyoung; Kang, Dahye; Han, Sang Hoon; Chun, Rina; Pandey, Ashok Kumar; Mishra, Neeraj Kumar; Hong, Sungwoo; Kim, In Su.
Angew Chem Int Ed Engl; 58(28): 9470-9474, 2019 Jul 08.
Artigo em Inglês | MEDLINE | ID: mdl-31069937
The ruthenium(II)-catalyzed C-H functionalization of (hetero)aryl azomethine imines with allylic acetals is described. The initial formation of allylidene(methyl)oxoniums from allylic acetals could trigger C(sp2 )-H allylation, and subsequent endo-type [3+2] dipolar cycloaddition of polar azomethine fragments to deliver valuable indenopyrazolopyrazolones. The utility of this method is showcased by the late-stage functionalization of bioactive molecules such as estrone and celecoxib. Combined experimental and computational investigations elucidate a plausible mechanism of this new tandem reaction. Notably, the reductive transformation of synthesized compounds into biologically relevant diazocine frameworks highlights the importance of the developed methodology.
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