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

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Title
Allylic Acetals as Acrolein Oxonium Precursors in Tandem C−H Allylation and [3+2] Dipolar Cycloaddition
Author(s)
Heeyoung Lee; Dahye Kang; Sang Hoon Han; Rina Chun; Ashok Kumar Pandey; Neeraj Kumar Mishra; Sungwoo Hong; In Su Kim
Publication Date
2019-07
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.58, no.28, pp.9470 - 9474
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, WeinheimThe 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
URI
https://pr.ibs.re.kr/handle/8788114/6060
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
H_Lee_et_al-2019-Angewandte_Chemie_International_Edition.pdfDownload

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