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

Author(s): Dieter Enders, Zai-Xin Chen.

Journal Name: Letters in Organic Chemistry

Volume 2 , Issue 2 , 2005

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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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Article Details

VOLUME: 2
ISSUE: 2
Year: 2005
Page: [156 - 159]
Pages: 4
DOI: 10.2174/1570178053202865
Price: $58

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