Diastereoselective hydroalkylation of aryl alkenes enabled by Remote hydride transfer

TETRAHEDRON

卷:76

Article

Gandamana, Dhika Aditya¹  Gagosz, Fabien²  Chiba, Shunsuke¹ 

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

[2] Univ Ottawa, Dept Chem & Biomol Sci, Ottawa, ON K1N 6N5, Canada

关键词: Hydride transfer;    Hydroalkylation;    1,2-Diastereoselectivity;    Catalysis;    Bronsted acid;   

DOI  :  10.1016/j.tet.2020.131272

来源: Elsevier

【 摘 要 】

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. (C) 2020 Elsevier Ltd. All rights reserved.

【 授权许可】

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