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Comprehensive Summary: We report herein a formal asymmetric epoxidation of arylalkanes enabled by a one‐pot dual‐catalysts system comprising a pincer Ir catalyst for alkane dehydrogenation‐alkene isomerization (AD‐ISO) and a chiral ketone catalyst for asymmetric alkene epoxidation. This protocol provides a catalytic method for the synthesis of aryl epoxides in useful yields with high regio‐ and stereoselectivity directly from readily available alkyl arenes. Stereospecific derivatizations of the epoxidation product allow access to various enantioenriched compounds. [ABSTRACT FROM AUTHOR]