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催化剂控制的Morita-Baylis-Hillman碳酸酯的发散分子内环化反应

Catalyst-Controlled Divergent Intramolecular Cyclizations of Morita-Baylis-Hillman Carbonates.

作者信息

Cai Wei, He Yanlin, Zhou Yiming, Huang You

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.

出版信息

J Org Chem. 2021 Sep 3;86(17):12267-12276. doi: 10.1021/acs.joc.1c01618. Epub 2021 Aug 23.

Abstract

Unprecedented catalyst-controlled divergent cyclizations of Morita-Baylis-Hillman carbonates have been established using either CsCO or quinuclidine as the catalyst. 1,2-Dihydroquinolines and 4-3,1-benzoxazines were efficiently synthesized via S2' and S2'-S2' processes, respectively. DFT calculations have led to a deeper understanding of these reaction modes and chemoselectivity.

摘要

使用碳酸铯或奎宁环作为催化剂,实现了前所未有的催化剂控制的Morita-Baylis-Hillman碳酸酯的发散环化反应。分别通过S2'和S2'-S2'过程高效合成了1,2-二氢喹啉和4,3,1-苯并恶嗪。密度泛函理论计算有助于更深入地理解这些反应模式和化学选择性。

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