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Curation of Computational Chemical Libraries Demonstrated with Alpha-Amino Acids
Published on: April 13, 2022
Oxidative α-Trichloromethylation of Tertiary Amines: An Entry to α-Amino Acid Esters
Changming Xu1,2, Zhaobin Zhu1, Yongchang Wang1
1School of Chemical and Biological Engineering , Lanzhou Jiaotong University , 88 Anning West Road , Lanzhou 730070 , China.
Abstract:
α-Trichloromethylation of tertiary amines with trimethyl(trichloromethyl)silane by oxidative coupling, using DDQ as an oxidant, has been realized. The reaction is instantaneous, is scalable, and tolerates a broad range of functional groups and heteroarenes. The trichloromethylated products can be easily converted into β,β-dichloroamines, enamines, and α-amino acid esters under operationally simple conditions. This methodology provides an efficient alternative to the poisonous cyanation reactions for the synthesis of carboxylic acid and their derivatives.
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