Redox-Neutral Access to Isoquinolinones via Rhodium(III)-Catalyzed Annulations of O-Pivaloyl Oximes with Ketenes

Xifa Yang; Song Liu; Songjie Yu; Lingheng Kong; Yu Lan; Xingwei Li

doi:10.1021/acs.orglett.8b00906

Redox-Neutral Access to Isoquinolinones via Rhodium(III)-Catalyzed Annulations of O-Pivaloyl Oximes with Ketenes

Org Lett. 2018 May 4;20(9):2698-2701. doi: 10.1021/acs.orglett.8b00906. Epub 2018 Apr 19.

Authors

Xifa Yang^{1

2}, Song Liu³, Songjie Yu¹, Lingheng Kong¹, Yu Lan³, Xingwei Li¹

Affiliations

¹ Dalian Institute of Chemical Physics , Chinese Academy of Sciences , Dalian 116023 , China.
² University of Chinese Academy of Sciences , Beijing 100049 , China.
³ School of Chemistry and Chemical Engineering , Chongqing University , Chongqing 400030 , China.

PMID: 29671601
DOI: 10.1021/acs.orglett.8b00906

Abstract

A mild and redox-neutral [4 + 2] annulation of O-pivaloyl oximes with ketenes has been realized for synthesis of quaternary-carbon-stereocenter-containing (QCSC) isoquinolinones, where the N-OPiv not only acts as an oxidizing group but also offers coordination saturation to inhibit protonolysis. The reaction mechanism has been studied by DFT calculations.

Publication types

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