A convenient procedure for the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides and alkenes.
[reaction: see text] Silver fluoride and cinchona alkaloids catalyze the diastereo- and enantioselective 1,3-dipolar cycloaddition between azomethine ylides, generated from N-alkylideneglycine esters, and acrylates to give the corresponding endo-adducts. Azomethine ylides derived from aromatic and aliphatic aldehydes react in a highly diastereoselective reaction with good yields and enantioselectivities of the substituted pyrrolidines.
Alemparte
Carlos
C
Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
Blay
Gonzalo
G
Jørgensen
Karl Anker
KA
D000179:Acrylates / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005998:Glycine / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000179:Acrylates; D000470:Alkaloids; D000475:Alkenes; D001391:Azo Compounds; D001597:Benzylidene Compounds; D005998:Glycine; C035956:methyl acrylate