Binaphthyl-Proline Hybrid Chiral Ligands: Modular Design, Synthesis, and Enantioswitching in Cu(II)-Catalyzed Enantioselective Henry Reactions

Autor: Chao Yao, Yaoqi Chen, Chao Wang, Ruize Sun, Haotian Chang, Ruiheng Jiang, Lin Li, Xin Wang, Yue-Ming Li
Rok vydání: 2022
Předmět:
Zdroj: The Journal of organic chemistry.
ISSN: 1520-6904
Popis: Chiral O-N-N tridentate ligands were designed from proline and BINOL. Their design strategy and performance were evaluated using a copper(II)-catalyzed asymmetric Henry reaction as a model. The desired β-nitroalcohols were obtained in up to 94% ee's. Preliminary results suggested that the stereofacial selection of the reactions was mainly controlled by the chiral diamine moiety derived from proline, and matching of the central and axial chiralities was essential for the high stereoselectivity of the reaction. Enantioswitching was observed when an appropriate substituent was introduced to the binaphthyl group.
Databáze: OpenAIRE