A novel type of highly efficient chiral C2-symmetric bipyridine-N,N’-dioxides ligands prepared from L-octahydroindole-2-carboxylic acid and successfully applied in the synthesis of optically pure 1,2,3-trisubstituted cyclopropanes employing sulfoxonium ylides with α,β-unsaturated 2-acyl imidazoles has been developed, affording the corresponding adducts in 88-98% yields with up to 99% enantioselectivity and >20:1 dr under mild conditions with broad scope. In addition, a scale-up experiment and the synthetic transformations of the cycloadducts further highlighted the synthetic utility.

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