Tetrahedron: Asymmetry

Chiral 1, 2, 4-triazoles: stereoselective acylation and chlorination

AR Katritzky, D Fedoseyenko, MS Kim, PJ Steel

文献索引：Katritzky, Alan R.; Fedoseyenko, Dmytro; Kim, Myong S.; Steel, Peter J. Tetrahedron Asymmetry, 2010 , vol. 21, # 1 p. 51 - 57

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被引用次数: 7

摘要

Acyl groups are transferred from diverse N-and O-acyl derivatives of chiral 3, 5-bis-(1- hydroxyethyl)-[1, 2, 4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee, depending on the temperature conditions and nature of the reagents. Thionyl chloride replaced the hydroxyl groups of (S)-1-[4-amino-5-((S)-1-hydroxy-ethyl)-[1, 2, 4]-triazol-3-yl]- ethanol 3 stereospecifically with inversion, as confirmed by X-ray analysis, which also ...