Regio- and Enantioselective C-H Cyclization of Pyridines with Alkenes Enabled by a Nickel/N-Heterocyclic Carbene Catalysis.
J Am Chem Soc
; 141(14): 5628-5634, 2019 04 10.
Article
en En
| MEDLINE
| ID: mdl-30888167
ABSTRACT
Annulated pyridines are ubiquitous scaffolds in many bioactive molecules. A highly regio- and enantioselective Ni(0)-catalyzed endo-selective C-H cyclization of pyridines with alkenes has been developed. An unprecedented enantioselective C-H activation at pyridyl 3- or 4-positions was enabled by bulky chiral N-heterocyclic carbene ligands. This protocol provides expedient access to a series of optically active 5,6,7,8-tetrahydroquinolines and 5,6,7,8-tetrahydroisoquinolines, compounds otherwise accessed with difficulty, in moderate to high yields (up to 99% yield) and enantioselectivities (up to 99% ee). To our knowledge, this is the first example of enantioselective C-H cyclization of pyridines to chiral annulated products.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Am Chem Soc
Año:
2019
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Article