Facile and stereoselective synthesis of non-racemic 3,3,3-trifluoroalanine

Marcello Crucianelli, Natalia Battista, Pierfrancesco Bravo, Alessandro Volonterio, Matteo Zanda

Research output: Contribution to journalArticlepeer-review

Abstract

A highly stereoselective enantiodivergent synthesis of non-racemic 3,3,3-trifluoroalanine 7 is reported. The methodology is based on the reduction, by 9-BBN or DIBAH, of the chiral sulfinimine 3 derived from ethyl trifluoropyruvate, followed by acidic hydrolysis of the resulting diastereomeric sulfinamides 4 and 5.

Original languageEnglish
Pages (from-to)1251-1258
Number of pages8
JournalMolecules
Volume5
Issue number12
Publication statusPublished - Dec 2000

Keywords

  • Amino acids
  • Asymmetric synthesis
  • Fluorine
  • Sulfinimines

ASJC Scopus subject areas

  • Organic Chemistry

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