Study of substrate dependence on the diastereoselectivity of the ruthenium(II) porphyrin catalyzed tandem formation and 1,3-dipolar cycloaddition reactions of carbonyl ylides

The effect of substrate substitution on reaction selectivity for the ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation/1,3-dipolar cycloaddition reaction of a variety of alkyl and aryl substituted alpha-diazo ketones 1 with pi-unsaturated compounds was examined. The results suggested the diastereoselectivity of the reaction to be highly substrate dependant. Similar yields and cis/trans selectivities have also been achieved for the analogous reactions with rhodium(II,II) dimer as catalyst.