Natural Product-Inspired Chiral Ligand Design: Aloperine and N-Substituted Aloperines-Induced Pd-Catalyzed Asymmetric Hydroarylation of Ketimines

A naturally occurring alkaloid aloperine was utilized as a chiral skeleton for the development of new ligands/catalysts in asymmetric synthesis. A number of N-substituted aloperines have been prepared, and a Pd-catalyzed asymmetric hydroarylation of ketimines using these chiral 1,3-diamine ligands was reported. A range of chiral sulfonyl amides were prepared in high yields and enantioselectivities. The stereoselectivity and structure relationships of aloperines have been studied. In addition, preliminary studies on the desymmetrization of meso-anhydride have also shown that these diamines have good potential in organocatalysis. These L discoveries would provide a new future development for natural product-inspired chiral ligand design and developments.

Automated summary

In this study, a naturally occurring alkaloid called aloperine was used as a chiral skeleton for the development of new ligands/catalysts in asymmetric synthesis. The Pd-catalyzed asymmetric hydroarylation using these chiral 1,3-diamine ligands showed high yields and enantioselectivities, indicating their potential in organocatalysis. This discovery opens up new possibilities in the design and development of natural product-inspired chiral ligands.