Facile and Stereoselective Synthesis of Non-Racemic 3,3,3-Trifluoroalanine

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.

Keywords

• Fluorine
• Amino acids
• Sulfinimines
• Asymmetric synthesis