Rhodium catalyzed asymmetric synthesis of Chiraphos derivatives

Herein, we report a highly efficient versatile synthetic route to Chiraphos derivatives through Rh/Ph-bod catalyzed asymmetric addition of aryl boronic acids to phosphinyl dienes. Various substituted phosphinyl dienes, both on the parent skeleton and the phosphine atoms, were well tolerated with this method and provided chiral phosphine oxides in satisfied yield and up to 95% ee. The corresponding Chiraphos derivative displayed an advantage over Chiraphos in the representative Pd-catalyzed asymmetric 1,4-addition reaction. (c) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

A highly efficient versatile synthetic route to Chiraphos derivatives has been reported through Rh/Ph-bod catalyzed asymmetric addition of aryl boronic acids to phosphinyl dienes. This method tolerated various substituted phosphinyl dienes and provided chiral phosphine oxides with satisfactory yield and high enantioselectivity. The resulting Chiraphos derivative exhibited an advantage in the representative Pd-catalyzed asymmetric 1,4-addition reaction.