[8+2] Formal Cycloaddition Reactions of Tropones with Azlactones under Brønsted Acid Catalysis and Synthesis of α‐(2‐Tropyl), α‐Alkyl α‐Amino Acids. Issue 7 (2nd January 2014)

• Record Type: Journal Article
• Authors: Esteban, Francisco; Alfaro, Ricardo; Yuste, Francisco; Parra, Alejandro; Ruano, José Luis García; Alemán, José
• Is Part Of: European journal of organic chemistry. Issue 7(2014)
• Page Start: 1395
• Page End: 1400
• Publication Date: 2014-01-02
• Subjects: Amino acids -- Tropones -- Cycloaddition -- Brønsted acids catalysis -- Heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301774
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The reaction of tropones with azlactones catalyzed by Brønsted acids affords a variety of dihydro‐2 H ‐cyclohepta[ b ]furan derivatives, corresponding to a formal [8+2] cycloaddition process. They can easily be opened by nucleophiles to afford a new type of α, α‐disubstituted α‐amino acid (or peptide) containing seven‐membered rings at the quaternary position. Abstract : The reaction of tropones with azlactones catalyzed by Brønsted acids affords a variety of dihydro‐2 H ‐cyclohepta[ b ]furan derivatives, corresponding to a formal [8+2] cycloaddition process. They can be easily opened by nucleophiles to afford a new type of α, α‐disubstituted α‐amino acid (or peptide) containing seven‐membered rings at the quaternary position.