Chemoselective syntheses of gamma-butyrolactams using vinyl sulfilimines and dichloroketene.
Reactions between vinyl sulfilimines and dichloroketene generated in situ from trichloroacetyl chloride in the presence of zinc-copper couple give mixtures of alpha-dichloro-gamma-butyrolactams and alpha-dichloro-gamma-butyrolactone imines. Fine-tuning of substituents within vinyl sulfilimines results in reactions with good chemoselectivity and yield for lactams.
Marino
Joseph P
JP
Department of Chemistry and Biochemistry, University of Notre Dame, Indiana 46556, USA. marino.12@nd.edu
Zou
Nanfei
N
D002384:Catalysis; D004000:Dichloroethylenes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D007769:Lactams / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D004000:Dichloroethylenes; D007097:Imines; D007769:Lactams; D013457:Sulfur Compounds; D014753:Vinyl Compounds; C039586:dichloroketene