New Chiral Auxiliaries for Enolate Alkylations

Kyu‐Sung ‐S Jeong, Kevin Parris, Pablo Ballester, Julius Rebek

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

The stereospecific synthesis (>99:1) of α‐alkylcarboxylic acids 3 has been achieved using chiral auxiliaries such as 1, which is a derivative of the Kemp triacid. Compound 1 is coupled at the imide group with the acid chloride 2. Lithiation (→enolate), alkylation, and cleavage leads to 3. The effectiveness of 1 is a consequence of the fact that it shields one side of the enolate from attack by the electrophile EX (examples: R  Me, E  PhCH2, or R  PhCH2, E  Me). (Figure Presented.)

Original languageEnglish
Pages (from-to)555-556
Number of pages2
JournalAngewandte Chemie International Edition in English
Volume29
Issue number5
DOIs
Publication statusPublished - 1990 May

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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