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

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Abstract

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.

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Journal

Journal ID (iso-abbrev): Org Lett

Title: Organic letters

Publisher: American Chemical Society (ACS)

ISSN (Electronic): 1523-7052

ISSN (Print): 1523-7052

Publication date (Electronic): Jul 02 2021

Volume: 23

Issue: 13

Affiliations

[1 ] Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, 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 210037, Jiangsu, China.

[3 ] Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.

[4 ] College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou 215123, P.R. China.

[5 ] Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan 010000, Republic of Kazakhstan.

[6 ] Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow 117198, Russia.

Article

DOI: 10.1021/acs.orglett.1c01590

PubMed ID: 34115493

SO-VID: d03f2c73-e6db-40f6-b3b9-956ec5d2592f

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