☆ 4.6 Review

Application of Metal-Free Dearomatization Reaction as a Sustainable Strategy to Direct Access Complex Cyclic Compounds

CHEMICAL RECORD (2023)

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Summary: Atom- and step-economy in IBX-assisted diversity-oriented synthesis is achieved with a versatile AQ auxiliary alpha-amino acid analogs, offering rapid access to polycyclic spiro-quinolines featuring a quaternary stereocenter in 20%-91% yields under mild conditions via 7,8-dearomatization of quinolines. The highlight of this intramolecular oxidation spiroannulation tandem reaction is the absence of a preinstalled activation group. These traditionally difficult-to-access N-heterospirocycles may provide a potentially interesting scaffold for synthetic and medicinal chemistry.

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