Borane-Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction-Induced Electrocyclization

Chemistry : a European Journal
Alexander F G MaierJan Paradies

Abstract

The borane-catalyzed synthesis of quinoline derivatives bearing tetrasubstituted stereocenters from vinyl anilines has been developed. Mechanistic studies and quantum-mechanical investigations support the hydride abstraction/electrocyclization/hydride addition mechanism. The products were obtained in up to 99 % yield with a diastereoselectivity of >99 % in favour for the 3a-5-cis isomer.

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Citations

May 23, 2020·Organic & Biomolecular Chemistry·Xiaoyu YangShuai-Shuai Li
Dec 17, 2020·Chemical Society Reviews·Yuanhong MaZhaomin Hou
Jan 23, 2021·Organic & Biomolecular Chemistry·Gautam KumarIndranil Chatterjee
Jul 7, 2020·Journal of the American Chemical Society·Jianbo Zhang, Sukbok Chang
May 29, 2019·The Journal of Organic Chemistry·Shuai ZhuJian Xiao
Jul 1, 2020·ACS Catalysis·Shyam BasakAlexander P Pulis
Mar 7, 2019·Organic Letters·Anirudra PaulDaniel Seidel
Jan 10, 2020·The Journal of Organic Chemistry·Yu-Quan ZhaoXiao-Chen Wang
May 24, 2019·Journal of the American Chemical Society·Anirudra Paul, Daniel Seidel
Jan 28, 2020·Organic Letters·Anirudra PaulDaniel Seidel

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