Chemo- and Enantioselective Insertion of Furyl Carbene into the N-H Bond of 2-Pyridones.
Angew Chem Int Ed Engl
; 60(31): 16942-16946, 2021 Jul 26.
Article
in En
| MEDLINE
| ID: mdl-34038015
ABSTRACT
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.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Angew Chem Int Ed Engl
Year:
2021
Document type:
Article
Affiliation country:
China