The invention provides cyclic alpha-dehydroamino ketones, chiral cyclic alpha-amino ketone and a preparation method of the chiral cyclic alpha-amino ketone. The preparation method comprises the following steps: enabling the cyclic alpha-dehydroamino ketones as shown in a general formula (1) to react in an organic solvent at a hydrogen atmosphere under the catalytic effect of diphosphine-rhodium complex to obtain the chiral cyclic alpha-amino ketone as shown in a general formula (2). The preparation method adopts an asymmetric catalytic hydrogenation, is simple and effective in process, and is suitable for industrial large-scale production. The product, chiral amino ketone, prepared according to the method can be further derived into chiral amino ketone alcohol ligand and chiral amino medicine intermediate, thus having wide application in the industry.