Diastereoselective hydroalkylation of aryl alkenes enabled by remote hydride transfer

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...

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Bibliographic Details
Main Authors: Gandamana, Dhika Aditya, Gagosz, Fabien, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2021
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Online Access:https://hdl.handle.net/10356/154141
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Institution: Nanyang Technological University
Language: English
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Summary: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.