Journal of the American Chemical Society, Vol.131, No.26, 9178-9178, 2009
Gold(I)-Catalyzed Enantioselective Ring Expansion of Allenylcyclopropanols
The asymmetric goid(I)-catatyzed ring expansion of 1-allenylcyclopropanots is described. The method provides synthetically valuable cyclobutanones with a vinyl-substituted quaternary stereogenic center in high enantiosetectivities and yields. The method shows a broad substrate scope, tolerating protected alcohols and amines, alkenes, unsaturated esters, and acetals. The reaction is easily adjustable to large-scale synthesis, leading to product formation without significant loss of selectivity or yield with only 0.5 mol% catalyst loading.