Enantioselective Synthesis of Trisubstituted Allenes via Cu(I)-Catalyzed Coupling of Aryldiazoalkanes with Terminal Alkynes

Chiral allenes are featured in as key structure units in many natural products and functional materials. They also serve as useful building blocks in organic synthesis and as chiral ligands/catalysts.[1] However, asymmetric synthesis of enantiomerically pure allenes is still in its infancy.[2] We have recently focused on the development of C-C bond forming reactions based on carbene-involved cross-coupling.[3] In this context, we has reported a novel synthesis of allenes from terminal alkynes and tosylhydrazones through the Cu(I)-catalyzed alkynyl migratory insertion.[4] Herein, we report our further effort to develop the asymmetric catalytic version of this coupling reaction with a newly designed chiral bisoxazoline ligand.Chiral allenes are featured in as key structure units in many natural products and functional materials. They also serve as useful building blocks in organic synthesis and as chiral ligands/catalysts.[1] However, asymmetric synthesis of enantiomerically pure allenes is still in its infancy.[2] We have recently focused on the development of C-C bond forming reactions based on carbene-involved cross-coupling.[3] In this context, we has reported a novel synthesis of allenes from terminal alkynes and tosylhydr中国化学会