Epoxy-annulations by reactions of alpha-amido ketones with vinyl sulfonium salts. Reagent versus substrate control and kinetic resolution.
Diphenyl vinyl sulfonium salt and chiral amido-ketones undergo highly diastereoselective epoxy-annulation reactions in good yield. The use of a chiral vinyl sulfonium salt dominates the stereochemical outcome of the annulation reaction (reagent control is greater than substrate control), and this has allowed the kinetic resolution of racemic amido-ketones to be achieved.
Unthank
Matthew G
MG
School of Chemistry, University of Bristol, Cantock's Close, Bristol, BS8 1TS United Kingdom.
Tavassoli
Bahareh
B
Aggarwal
Varinder K
VK
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D012492:Salts; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D004852:Epoxy Compounds; D007659:Ketones; D011759:Pyrrolidines; D012492:Salts; D013452:Sulfonium Compounds; D014753:Vinyl Compounds