Enantioselective Synthesis of Aminoindan Carboxylic Acid Derivatives by the Catalytic Intramolecular [2+2+2] Cycloaddition of Amino-Acid-Tethered Triynes

Yu Ki Tahara, Shuhei Obinata, Stephen Kyalo Kanyiva, Takanori Shibata, Attila Mándi, Tohru Taniguchi, Kenji Monde

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The enantioselective synthesis of aminoindan carboxylic acid (Aic) derivatives was achieved by Rh-catalyzed intramolecular [2+2+2] cycloaddition of amino-acid-tethered triynes. This reaction, along with recrystallization, gave chiral tethered Aic derivatives with excellent enantiomeric excess. Subsequent hydrolysis of the tethered Aic compounds afforded chiral Aic derivatives, which were further transformed into a free Aic and its dimethyl ester in good yields.

Original languageEnglish
Pages (from-to)1405-1413
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number7
DOIs
Publication statusPublished - 2016 Mar 1

Keywords

  • Amino acids
  • Cycloaddition
  • Enantioselectivity
  • Rhodium

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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