Synthesis of optically active α-(nonafluoro-tert-butoxy)carboxylic acids

Tamás Csóka, Anikó Nemes, Dénes Szabó

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Three novel α-(nonafluoro-tert-butoxy)carboxylic esters were synthesized by two methods: the Mitsunobu reaction of optically active (S)-α-hydroxycarboxylic esters and the Williamson synthesis starting from the corresponding O-mesyl derivatives. Both procedures from ethyl (S)-lactate resulted in the formation of a fluorous optically active (R)-lactic acid ester derivative, while the reactions from methyl (S)-mandelate took place with racemization. The proposed mechanism of this racemization is described. The conversion of methyl (S)-phenyllactate under Mitsunobu conditions was also stereospecific, but the reaction of its O-mesyl derivative yielded a mixture of substitution and elimination products. The optical purity of the α-(nonafluoro-tert-butoxy)carboxylic acids prepared by the hydrolysis of the above esters was determined by 1H NMR spectroscopy.

Original languageEnglish
Pages (from-to)1730-1733
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number13
DOIs
Publication statusPublished - Mar 27 2013

Keywords

  • Chiral carboxylic acid
  • Fluorous tag
  • Mitsunobu reaction
  • Nonafluoro-tert-butoxy

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of optically active α-(nonafluoro-tert-butoxy)carboxylic acids'. Together they form a unique fingerprint.

  • Cite this