Hydrolytic enantioselective protonation of cyclic dienyl esters and a β-diketone with chiral phase-transfer catalysts

Eiji Yamamoto, Daichi Gokuden, Ayano Nagai, Takashi Kamachi, Kazunari Yoshizawa, Akiyuki Hamasaki, Tamao Ishida, Makoto Tokunaga

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

Hydrolytic enantioselective protonation of dienyl esters and a β-diketone catalyzed by phase-transfer catalysts are described. The latter reaction is the first example of an enantio-convergent retro-Claisen condensation. Corresponding various optically active α,β-unsaturated ketones having tertiary chiral centers adjacent to carbonyl groups were obtained in good to excellent yields and enantiomeric ratios (83-99%, up to 97.5:2.5 er).

Original languageEnglish
Pages (from-to)6178-6181
Number of pages4
JournalOrganic letters
Volume14
Issue number24
DOIs
Publication statusPublished - Dec 21 2012

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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