Synthesis of β-Benzylsulfanyl-β-trifluoromethyl-α-amino Acids Via Michael Addition in the Presence of Et3N/LiBr

Title: Synthesis of β-Benzylsulfanyl-β-trifluoromethyl-α-amino Acids Via Michael Addition in the Presence of Et3N/LiBr

Volume: 2 Issue: 2

Author(s): Dieter Enders and Zai-Xin Chen

Affiliation:

Keywords: fluorinated amino acids, sulfur substituted amino acids, michael addition, dehydroamino acid esters, bifunctional catalyst, mercaptanes

Abstract: β-Benzylsulfanyl-β-trifluoromethyl-α-amino acid esters have been synthesized from (Z)-β- substituted-β-trifluoromethyl-α,β-dehydroamino acid esters via Michael addition with moderate diastereoselectivities. The reaction was investigated with various catalysts. Et3N and LiBr gave satisfactory results, which operated synergistically as bifunctional catalyst. However, the other tested chiral catalysts gave no good enantioselectivities.

Cite this article as:

Enders Dieter and Chen Zai-Xin, Synthesis of β-Benzylsulfanyl-β-trifluoromethyl-α-amino Acids Via Michael Addition in the Presence of Et3N/LiBr, Letters in Organic Chemistry 2005; 2 (2) . https://dx.doi.org/10.2174/1570178053202865