Palladium-Catalyzed Arylative Dearomatization and Subsequent Aromatization/Dearomatization/Aza-Michael Addition: Access to Zephycarinatine and Zephygranditine Skeletons

We have developed a novel palladium-catalyzed arylative dearomatization and subsequent aromatization/dearomatization/aza-Michael addition process of Ugi adducts, enabling the rapid construction of diverse zephycarinatine and zephygranditine scaffolds containing two adjacent quaternary carbon stereocenters with excellent chemoselectivity and stereoselectivity in a rapid, step-economical, and highly efficient manner. This approach shows broad substrate scope and excellent functional-group tolerance with diverse electron-rich and electron-deficient aromatic substrates. The synthetic utility of this method is further demonstrated by versatile transformations of the products. © 2021 American Chemical Society.

Authors
Liu C.1 , Song L.2 , Van Meervelt L. , Peshkov V.A.4, 5 , Li Z.1 , Van Der Eycken E.V.
Journal
Organic Letters
Language
English
Status
Published
Link
External link
DOI
10.1021/ACS.ORGLETT.1C01590
Year
2021
Organizations
  • 1 Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, Ku Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 2 Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing, Jiangsu, 210037, China
  • 3 Biomolecular Architecture, Department of Chemistry, Ku Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 4 College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, China
  • 5 Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan, 010000, Kazakhstan
  • 6 Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
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