Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid

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外文摘要：Catalytic enantioselective alkenylation is an efficient method to construct chiral alkene molecules,but the asymmetric alkenylation of simple alkenes catalyzed by metal-free catalysts remains an elusive chal-lenge.Herein,we reported an asymmetric alkenylation of benzoxazinones with diarylethylenes by uti-lizing a B(C6F5)3/chiral phosphoric acid catalyst.A broad of benzoxazinones and diarylethylenes with electron-withdrawing and electron-donating groups were tolerated(up to 95％yield and 97.5∶2.5 e.r.)in the methodology under mild reaction conditions.Moreover,the synthetic utility was confirmed by the scaled-up reaction and transformations of the products.The mechanism was preliminarily explored by control reactions,nonlinear effect experiment and DFT calculations.

外文关键词：

Asymmetric alkenylationSimple alkenesBenzoxazinonesB(C6F5)3/chiral phosphoric acidTheoretical calculations

作者：

Zhen Liu、Zhi-Yuan Ren、Chen Yang、Xiangyi Shao、Li Chen、Xin Li

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作者单位：

State Key Laboratory of Elemento-Organic Chemistry,Frontiers Science Center for New Organic Matter,College of Chemistry,Nankai University,Tianjin 300071,China

Zhenhai High School of Zhejiang,Ningbo 315299,China

Haihe Laboratory of Sustainable Chemical Transformations,Tianjin 300192,China

基金：

国家自然科学基金国家自然科学基金国家自然科学基金National Science and Technology Fundamental Resource Investigation Program of China

项目编号：

2219301121971120219330082018FY201200

出版年：

2024

DOI：

10.1016/j.cclet.2023.108939

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCD

影响因子：0.771

ISSN：1001-8417

年,卷(期)：2024.35(5)

参考文献量60