A Fresh Look at the Staudinger Reaction on Azido Esters: Formation of 2H-1,2,3-Triazol-4-ols from α-Azido Esters Using Trialkyl Phosphines

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• 作者：Scott D. Taylor ; Chuda Raj Lohani
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：18
• 期：17
• 页码：4412-4415
• 全文大小：309K
• 年卷期：0
• ISSN：1523-7052

文摘

Phenyl esters of α-azido acids react with trialkylphosphines in THF/H₂O to give 5-substituted 2H-1,2,3-triazol-4-ols in good to excellent yields. In contrast, their reaction with PPh₃ in THF/H₂O give the amino esters as the major product and no triazoles. Reaction between an α-azido phenyl ester and P(OEt)₃ provided the corresponding phosphoramidate in excellent yield, but no triazole was formed.