Umpolung of o-Hydroxyaryl Azomethine Ylides: Entry to Functionalized γ-Aminobutyric Acid under Phosphine Catalysis.

Org Lett

State Key Laboratory of Natural Medicines, Department of Organic Chemistry , China Pharmaceutical University, Nanjing , 210009 , China.

Published: September 2018

A phosphine-catalyzed reaction between o-hydroxyaryl azomethine ylides and MBH carbonates provides access to highly functionalized γ-aminobutyric acid derivatives in moderate to good yields. Mechanistically, the reaction involves a phosphine-catalyzed tandem S2'/2-aza-Cope rearrangement/intramolecular addition process.

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http://dx.doi.org/10.1021/acs.orglett.8b02297DOI Listing

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