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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 2, Issue 2, 2005

Page: [156 - 159] Pages: 4

DOI: 10.2174/1570178053202865

Price: $65

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.

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


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