Phosphorus molecules bearing a chiral center on the P-atom, also known as P-stereogenic compounds, feature many peculiar properties, allowing their use in various fields of applications, ranging from chemistry to biology. P-chiral secondary phosphines, an important class of P-stereogenic compounds, serve as versatile building blocks for the divergent construction of chiral phosphorus ligands and transition metal complexes. However, the reported methods limit to the resolution of secondary phosphine chiral at phosphorus via recrystallization or using chiral auxiliaries.
Recently, Wei-Liang Duan group (College of Chemistry and Chemical Engineering, Yangzhou University) reported for the first time the catalytic synthesis of P-stereogenic secondary phosphines with high enantio- and diastereoselectivities in the presence of a newly developed unsymmetric bisphosphine pincer-nickel complex (J. Am. Chem. Soc. 2021, 143, 5685–5690). The catalytic manifold is endowed with good functional group tolerance and reaction scalability and the resulting chiral secondary phosphines are readily convertible into useful chiral phosphines ligands for asymmetric transformations. They anticipate that the catalytic method will simplify the synthesis of P-stereogenic compounds in enantioselective catalysis and medicine.
This work was published by J. Am. Chem. Soc. (https://pubs.acs.org/doi/10.1021/jacs.1c02772).
Corresponding Authors are Chuanyong Wang and Wei-Liang Duan. The experiments were carried out by Kesheng Huang and Jie Ye.
This work was financially supported by the National Natural Science Foundation of China (21801220, 21672183, and 22071139), the Natural Science Foundation of Jiangsu Province (BK20180892), the Priority Academic Program Development of Jiangsu Higher Education Institutions, and Top-notch Academic Programs Project of Jiangsu Higher Education Institutions.