In summary, a selenium-p-acid-catalyzed regiocontrolled olefin transpositional allylic chlorination and imidation were developed. The reaction outcome benefits from a B(MIDA) substitution. And the stabilization of a-anion from a hemilabile B(MIDA) moiety was believed to be the key factor for selectivity, which facilitates the irreversible selenium-mediated syn-H elimination. The protocol led to the synthesis of a wide array of multifunctional amphoteric building blocks with both the olefin and boron functionality being preserved as valuable handles for further chemical elaboration. The utilities of the products were demonstrated. The unique effect of B(MIDA) revealed in this protocol may inspire more interesting boron chemistry from the synthetic community. Basic and Applied Basic Re-search Foundation (2020A1515010624), the Fundamental Research Funds for the Central Universities (20ykzd12) and the Local Innovative and Research Teams Project of Guangdong Pearl River Talents Program (2017BT01Y093).