Chemo- and Enantioselective Insertion of Furyl Carbene into the N-H Bond of 2-Pyridones.
Kai WangZiye LiuGuangyang XuYing ShaoShengbiao TangPing ChenXinhao ZhangJiangtao SunPublished in: Angewandte Chemie (International ed. in English) (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.
Keyphrases
- quantum dots
- density functional theory
- photodynamic therapy
- ionic liquid
- cancer therapy
- locally advanced
- molecular dynamics
- molecular dynamics simulations
- combination therapy
- room temperature
- electron transfer
- molecular docking
- highly efficient
- radiation therapy
- metal organic framework
- crystal structure
- carbon dioxide