71104-26-2Relevant academic research and scientific papers
Chemo- and Enantioselective Insertion of Furyl Carbene into the N?H Bond of 2-Pyridones
Chen, Ping,Liu, Ziye,Shao, Ying,Sun, Jiangtao,Tang, Shengbiao,Wang, Kai,Xu, Guangyang,Zhang, Xinhao
, p. 16942 - 16946 (2021)
Asymmetric carbene insertion reactions represent one of the most important protocols to construct carbon–heteroatom bonds. The use of donor–acceptor diazo compounds bearing an ester group is however a prerequisite for achieving high enantioselectivity. Herein, we report a chemo- and enantioselective formal N?H insertion of 2-pyridones that has been accomplished for the first time with enynones as the donor–donor carbene precursors. DFT calculations indicate an unprecedented enantioselective 1,4-proton transfer from O to C. The rhodium catalyst provides a chiral pocket in which the steric repulsion and the π–π interaction of the propeller ligand play a critical role in determining the selectivities.
