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

Xifa YangSong LiuSongjie YuLingheng KongYu Lan Xingwei Li

Published in: Organic letters (2018)

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.

Keyphrases

density functional theory
electron transfer
molecular dynamics
molecular dynamics simulations
room temperature
monte carlo
crystal structure