Affiliation:
1. Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering Feringa Nobel Prize Scientist Joint Research Center Frontiers Science Center for Materiobiology and Dynamic Chemistry School of Chemistry and Molecular Engineering East China University of Science & Technology Shanghai 200237 China
2. Shanghai Frontiers Science Center of Biomimetic Catalysis Shanghai Normal University Shanghai 200234 China
Abstract
AbstractAxially chiral biaryl δ‐amino acids possess significantly different conformational properties and chiral environment from centrally chiral amino acids, therefore, have drawn considerable attention in the fields of synthetic and medicinal chemistry. Herein, a novel chiral phenanthroline‐potassium catalyst has been developed by constructing a well‐organized axially chiral ligand composed of one 1,10‐phenanthroline unit and two axially chiral 1,1′‐bi‐2‐naphthol (BINOL) units. In the presence of this catalyst, good to excellent yields and enantioselectivities (up to 99 % yield, 98 : 2 er) have been achieved in the ring‐opening alcoholytic dynamic kinetic resolution of a variety of biaryl lactams, thereby providing an efficient protocol for catalytic asymmetric synthesis of unnatural axially chiral biaryl δ‐amino acid derivatives.
Funder
National Natural Science Foundation of China
Fundamental Research Funds for the Central Universities
Project 211