A new copper-catalyzed [3 + 2] cycloaddition: enantioselective coupling of terminal alkynes with azomethine imines to generate five-membered nitrogen heterocycles.
A copper-catalyzed method for the regioselective 1,3-dipolar cycloaddition of azomethine imines to terminal alkynes has been developed. Through the use of a chiral phosphaferrocene-oxazoline ligand, a wide range of substrates can be coupled to generate useful heterocycles in very good enantiomeric excess.
Shintani
Ryo
R
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Fu
Gregory C
GC
D000480:Alkynes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D001391:Azo Compounds; D006571:Heterocyclic Compounds; D007097:Imines; D003300:Copper