Synthesis of oxime ethers via a formal reductive O–H bond insertion of oximes to α-keto esters

Abstract

This study describes an efficient approach to access oxime ethers via P(III)-mediated O–H bond insertion reaction of oximes with α-keto esters. The strategy involves the protonation of in situ generated Kukhtin–Ramirez adducts, followed by S_N2-type reaction. Important features include a good functional group tolerance, operational simplicity, and application to gram scale synthesis and the synthesis of an acaricide.