Palladium-Catalyzed Asymmetric (2+3) Annulation of p -Quinone Methides with Trimethylenemethanes: Enantioselective Synthesis of Functionalized Chiral Spirocyclopentyl p -Dienones

A novel asymmetric catalytic (2+3) annulation of -quinone methides with CN-substituted trimethylenemethane is described under palladium catalysis, providing an alternative approach for the enantioselective construction of highly functionalized chiral spirocyclopentyl -dienones. Driven by the signifi...

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Bibliographic Details
Published in:Organic letters 2020-06, Vol.22 (11), p.4171-4175
Main Authors: Jia, Zhi-Long, An, Xian-Tao, Deng, Yu-Hua, Wang, Hui-Bin, Gan, Kang-Ji, Zhang, Jing, Zhao, Xian-He, Fan, Chun-An
Format: Article
Language:English
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Summary:A novel asymmetric catalytic (2+3) annulation of -quinone methides with CN-substituted trimethylenemethane is described under palladium catalysis, providing an alternative approach for the enantioselective construction of highly functionalized chiral spirocyclopentyl -dienones. Driven by the significant improvement in the reactivity and enantioselectivity, a novel type of non- -symmetric phosphoramidite ligand from the chirality-matched combination of ( )-BINOL and sterically demanding amine derived from l-hydroxyproline is evolved and explored for the protocol presented here.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01252