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膦催化对喹胺与森田-贝利斯-希尔曼碳酸酯的多米诺[3 + 3]环化反应:合成氢喹啉衍生物

Phosphine-Catalyzed Domino [3 + 3] Cyclization of para-Quinamines with Morita-Baylis-Hillman Carbonates: Access to Hydroquinoline Derivatives.

作者信息

Jin Hongxing, Lai Jingxiong, Huang You

机构信息

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

Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071 , China.

出版信息

Org Lett. 2019 Apr 19;21(8):2843-2846. doi: 10.1021/acs.orglett.9b00834. Epub 2019 Mar 27.

Abstract

A phosphine-catalyzed [3 + 3] cyclization strategy between para-quinamines and HCHO Morita-Baylis-Hillman (MBH) carbonates was discovered, delivering a series of highly functionalized hydroquinoline derivatives in moderate to good yields and excellent diastereoselectivity. Moreover, mechanistic insights, gram-scale experiments, and synthetic manipulations of the products were also discussed.

摘要

发现了一种膦催化的对喹胺与甲醛的森田-贝利斯-希尔曼(MBH)碳酸酯之间的[3 + 3]环化策略,以中等至良好的产率和优异的非对映选择性得到了一系列高度官能化的氢喹啉衍生物。此外,还讨论了机理见解、克级实验以及产物的合成操作。

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