Generation and Reaction of Carbamoyl Anions in Flow: Applications in the Three-Component Synthesis of Functionalized α-Ketoamides

Aiichiro Nagaki; Yusuke Takahashi; Jun-Ichi Yoshida

doi:10.1002/anie.201601386

Generation and Reaction of Carbamoyl Anions in Flow: Applications in the Three-Component Synthesis of Functionalized α-Ketoamides

Angew Chem Int Ed Engl. 2016 Apr 18;55(17):5327-31. doi: 10.1002/anie.201601386. Epub 2016 Mar 15.

Authors

Aiichiro Nagaki¹, Yusuke Takahashi², Jun-Ichi Yoshida³

Affiliations

¹ Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan. anagaki@sbchem.kyoto-u.ac.jp.
² Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
³ Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan. yoshida@sbchem.kyoto-u.ac.jp.

PMID: 26990703
DOI: 10.1002/anie.201601386

Abstract

Using a flow microreactor system, carbamoyllithium compounds were successfully generated and used for reactions with electrophiles to give various amides, including α-ketoamides. The present method could be applied to the three-component synthesis of functionalized α-ketoamides using a carbamoyllithium compound, methyl chloroformate, and a functionalized organolithium reagent.

Keywords: amides; carbonyl groups; flow chemistry; lithiation; microreactors.

Publication types

Research Support, Non-U.S. Gov't