Dynamic Kinetic Resolution Processes Based on the Switchable Configurational Instability of Allenyl Copper Reagents.
Chayma Ben MaamerPierre C MpawenayoBaptiste LecacheyNacira AlouanePierre MangeneyArie Van der LeeJérôme MarrotSamira BouaouliMaya GuillaumontRafâa BesbesHélène GerardEmmanuel VranckenJean-Marc CampagnePublished in: Organic letters (2021)
The configurational instability of allenyl copper reagents is unveiled. An experimental study highlights the crucial role of Li+ and of the reaction temperature in the control of the configurational stability of allenyl copper reagents. A judicious choice of the reaction conditions allows efficient dynamic kinetic resolution processes and gives a one-pot access to homopropargylic alcohols or amines bearing up to four contiguous defined stereogenic centers.