The development of chiral hypervalent iodine-catalyzed oxidative transformations is one of the most challenging areas in asymmetric organocatalysis. Although several elegant chiral hypervalent iodine(III and V) reagents or catalysts had been developed for various asymmetric oxidation reactions, the enantioselectivities had been moderate before our paper was published in 2010. We have had a great interest in the development of organocatalysis based on hypervalent chemistry since 2007. In this account, we describe our design concept of conformationally-flexible chiral hypervalent organoiodine(III), and the results obtained for catalytic use of our chiral iodines(III) for enantioselective Kita oxidative spirolactonization. Additionally, other chiral hypervalent iodine-mediated asymmetric oxidation reactions reported after our publications are also highlighted briefly.