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

Norihiko Takeda; Ryoya Maeda; Motohiro Yasui; Masafumi Ueda

doi:10.1039/d3cc05522a

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

Chem Commun (Camb). 2023 Dec 21;60(2):172-175. doi: 10.1039/d3cc05522a.

Authors

Norihiko Takeda¹, Ryoya Maeda¹, Motohiro Yasui¹, Masafumi Ueda¹

Affiliation

¹ Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan. masa-u@kobepharma-u.ac.jp.

PMID: 38053438
DOI: 10.1039/d3cc05522a

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.