Stereoselective synthesis of highly substituted Delta1-pyrrolines: exo-selective 1,3-dipolar cycloaddition reactions with azlactones.
We report herein a silver(I)-catalyzed exo-selective synthesis of highly substituted Delta1-pyrroline scaffolds from amino acid-derived münchnones. Silver acetate successfully catalyzed the cycloaddition reaction of azlactones with alkenes, generating Delta1-pyrrolines in very good yields without isomerization to the Delta2-pyrrolines or decarboxylation.
Peddibhotla
Satyamaheshwar
S
Department of Chemistry, Michigan State University, East Lansing, MI 48823, USA.
Tepe
Jetze J
JJ
D000475:Alkenes / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007783:Lactones / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D001372:Aza Compounds; D007783:Lactones; D011758:Pyrroles; C015485:delta-1-pyrroline-5-carboxylate; D012834:Silver