Chemo- And Enantioselective Insertion Of Furyl Carbene Into The N-H Bond Of 2-Pyridones
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2021)
摘要
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 pi-pi interaction of the propeller ligand play a critical role in determining the selectivities.
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关键词
2-pyridone, asymmetric catalysis, carbene, insertion, proton transfer
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