PhI(OAc)2-promoted umpolung acetoxylation of enamides for the synthesis of α-acetoxy ketones

作者:Chen, Ming; Zhang, Wei; Ren, Zhi-Hui; Gao, Wen-Yun; Wang, Yao-Yu; Guan, Zheng-Hui*
来源:Science China Chemistry, 2017, 60(6): 761-768.
DOI:10.1007/s11426-016-0478-3

摘要

Umpolung is a fundamental concept in organic chemistry, which provides an alternative strategy for the synthesis of target compounds which were not easily accessible by conventional methods. Herein, a mild and efficient PhI(OAc)(2)-promoted umpolung acetoxylation reactions of enamides was developed for the synthesis of alpha-acetoxy ketones. The reaction tolerates a wide range of functional groups and affords alpha-acetoxy ketones in good to excellent yields. PhI(OAc)(2) serves as a source of acetoxy in the reaction.