Hypervalent iodine reagents allow transformations under very mild reaction conditions. They are not only environmentally friendly oxidizing agents used in a wide range of transformations, but can also serve in highly selective asymmetric transformations which can be easily achieved using these reagents. The development of novel asymmetric metal-free transformations will lead to novel and powerful stereoselective protocols. Such advancements are still very much sought after for many transformations in organic synthesis and will be used by the fine chemical and pharmaceutical industries. The challenge of developing new metal-free approaches with chiral hypervalent iodine reagents is considerable as efficient procedures of this type are still in their infancy. We will develop novel and efficient enantiomerically pure hypervalent reagents/catalysts for such reactions. Iodonium ylide chemistry and utilization of suitable chiral iodonium ylides will be developed for the metal-free carbene transfer from iodonium ylides to carbon – nitrogen double bonds. Along with the successful development and application in asymmetric transformations, we will focus on the continuous-flow synthesis of complex molecules in which iodine reagent oxidation is one of the key steps. Self-optimization of reaction conditions through incorporation of analytical methods will be pursued.