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Diastereoselective hydroalkylation of aryl alkenes enabled by Remote hydride transfer

Abstract Leveraging of 1,5-hydride shift enabled diastereoselective hydroalkylation of aryl alkenes, allowing for construction of consecutive vicinal stereogenic centers in a single process. The transformation is triggered by electrophilic alkylation… Click to show full abstract

Abstract Leveraging of 1,5-hydride shift enabled diastereoselective hydroalkylation of aryl alkenes, allowing for construction of consecutive vicinal stereogenic centers in a single process. The transformation is triggered by electrophilic alkylation of aryl alkenes with in-situ generated carbocations, that is followed by diastereoselective 1,5-hydride shift to the resulting benzylic carbocation through a rigid 6-membered ring chair-like transition state.

Keywords: hydride; diastereoselective hydroalkylation; aryl alkenes; aryl; hydroalkylation aryl

Journal Title: Tetrahedron
Year Published: 2020

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