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Following the success of the first intermolecular cyclopropanations of diazo acetoxy acetone with olefins using a novel p-nitro-Ru(II)-diphenyl-Pheox catalyst, other α-functionalized diazoketones have synthesized using the same reaction conditions. Consequently, chiral cyclopropyl products were formed with excellent yield (up to 87% yield), high diastereoselectivity (up to 99:1), and high enantioselectivity (up to 90% ee).