Enantioselective synthesis of cyclic α-aminoboronates via copper-catalyzed dearomative borylation of 4-quinolinols

A highly enantioselective and regioselective dearomative borylation of 4-quinolinols was developed using a Cu(i)/(R,R)-Ph-BPE catalyst for efficient synthesis of unprecedented heterocyclic alpha-amino boronates, a new class of compounds potentially relevant to drug discovery, in generally excellent yields and enantioselectivities. The products were also useful intermediates for highly functionalized tetrahydroquinolines and cyclic alpha-aminoboronate derivatives.

Automated summary

A highly enantioselective and regioselective dearomative borylation method was developed for the synthesis of unprecedented heterocyclic alpha-amino boronates. The products can serve as useful intermediates for highly functionalized tetrahydroquinolines and cyclic alpha-aminoboronate derivatives.