Journal
ORGANIC LETTERS
Volume 23, Issue 13, Pages 5065-5070Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01590
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Funding
- FWO (Fund for Scientific Research-Flanders)
- NSFC (National Natural Science Foundation) of China [GMD-D5996-G0E5319N]
- RUDN University Strategic Academic Leadership Program
- China Scholarship Council (CSC)
- Hercules Foundation [AKUL/09/0035]
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This novel palladium-catalyzed method allows for the rapid construction of diverse zephycarinatine and zephygranditine scaffolds with two adjacent quaternary carbon stereocenters in a rapid, step-economical, and highly efficient manner. It demonstrates broad substrate scope and excellent functional-group tolerance with various electron-rich and electron-deficient aromatic substrates, showing great synthetic utility through versatile transformations of the products.
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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