Abstract

A method for the preparation of 5-aminobutenolides from 2-bromo-2H-azirine-2-carboxylic esters/amides with arylacetic acids has been developed. The reaction regioselectivity can be switched by a change of the basic catalyst, making it possible to prepare both butenolide-based α- and β-amino acid derivatives. The change in the regioselectivity is interpreted in terms of the stability and reactivity of the enolates formed during the SN2′ substitution of the bromine in the azirine by the carboxylate ion.

Original languageEnglish
Pages (from-to)3023-3027
Number of pages5
JournalOrganic Letters
Volume22
Issue number8
DOIs
Publication statusPublished - 31 Mar 2020

Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Regiodivergent Synthesis of Butenolide-Based α- And β-Amino Acid Derivatives via Base-Controlled Azirine Ring Expansion'. Together they form a unique fingerprint.

Cite this