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[8+2] Formal Cycloaddition Reactions of Tropones with Azlactones under Brønsted Acid Catalysis and Synthesis of α‐(2‐Tropyl), α‐Alkyl α‐Amino Acids
Author(s) -
Esteban Francisco,
Alfaro Ricardo,
Yuste Francisco,
Parra Alejandro,
Ruano José Luis García,
Alemán José
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301774
Subject(s) - chemistry , cycloaddition , furan , nucleophile , brønsted–lowry acid–base theory , alkyl , catalysis , organic chemistry , amino acid , medicinal chemistry , biochemistry
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.