Application of α-Trifluoromethyl Ketone Participated Three-Component Reaction for the N-Fluorinated Vinyl Ether Functionalization of α-Amino Acids

doi:10.6023/cjoc202607006

Abstract

The N-center functionalization of amino acid is crucial for improving the function of amino acids and peptides. Traditional methods for such functionalization usually rely on the transition metal catalysis, high temeprature or strong oxidant, leadin to problems such as high cost, low functional group tolerance an the racemization of the chiral center etc. Herein, we present a three-component protocol involving α-trifluoromethyl ketones, HIFP and α-amino acid esters, enabling the multiple deflurination under base promotion for the construction of α-amino acid derivatives featuring N-hexafluoroisopropyl vinyl structure. The reaction proceeds under metal- and oxidant-free conditions, providing mild and novel mild protocl for the new functionalization of amino acids in the N-center.

Key words: three-component, HIFP, defluorination, amino acid functionalization

Cite this article

Song, Huanhuan, Wan, Changfeng, Liu, Yunyun, Zhang, Wen-Bo, Wan, Jie-Ping. Application of α-Trifluoromethyl Ketone Participated Three-Component Reaction for the N-Fluorinated Vinyl Ether Functionalization of α-Amino Acids[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202607006.

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