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

作者：Taylor Scott D^*; Lohani Chuda Raj

来源：Organic Letters, 2016, 18(17): 4412-4415.

DOI：10.1021/acs.orglett.6b02204

Phenyl esters of alpha-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 alpha-azido phenyl ester and P(OEt)(3) provided the corresponding phosphoramidate in excellent yield, but no triazole was formed.

• 出版日期2016-9-2