All-Carbon Quaternary Stereocenters α to Azaarenes via Radical-Based Asymmetric Olefin Difunctionalization.

Yanli Yin, Yunqiang Li, Theo Goncalves, Qiangqiang Zhan, Guanghui Wang, Xiaowei Zhao, Baokun Qiao, Kuo-Wei Huang, Zhiyong Jiang

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Abstract

A radical-based asymmetric olefin difunctionalization strategy for rapidly forging all-carbon quaternary stereocenters α to diverse azaarenes is reported. Under cooperative photoredox and chiral Brønsted acid catalysis, cyclopropylamines with α-branched 2-vinylazaarenes can undergo a sequential two-step radical process, furnishing various valuable chiral azaarene-substituted cyclopentanes. The use of the rigid and confined C2-symmetric imidodiphosphoric acid catalysts achieves high enantio- and diastereo-selectivities for these asymmetric [3 + 2] cycloadditions.
Original languageEnglish (US)
JournalJournal of the American Chemical Society
DOIs
StatePublished - Nov 5 2020

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  • CCDC 1959654: Experimental Crystal Structure Determination : 2-(2-oxo-1-phenylcyclopentan-1-yl)pyridine N-oxide

    Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator), Huang, K. (Creator), Jiang, Z. (Creator), Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator), Jiang, Z. (Creator), Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator), Jiang, Z. (Creator), Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator), Jiang, Z. (Creator), Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator) & Jiang, Z. (Creator), Cambridge Crystallographic Data Centre, Nov 12 2020

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  • CCDC 1959655: Experimental Crystal Structure Determination : N-[2-(4-bromophenyl)-2-(1-methyl-1H-imidazol-2-yl)cyclopentyl]aniline

    Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator), Huang, K. (Creator), Jiang, Z. (Creator), Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator), Jiang, Z. (Creator), Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator), Jiang, Z. (Creator), Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator), Jiang, Z. (Creator), Yin, Y. (Creator), Li, Y. (Creator), Goncalves, T. (Creator), Zhan, Q. (Creator), Wang, G. (Creator), Zhao, X. (Creator), Qiao, B. (Creator) & Jiang, Z. (Creator), Cambridge Crystallographic Data Centre, Nov 12 2020

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