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Title: Desymmetrization of cyclic 1,3-Diketones under N-Heterocyclic carbene organocatalysis: access to organofluorines with multiple stereogenic centers
Authors: Wang, Guanjie
Zhang, Min
Guan, Yezhi
Zhang, Ye
Hong, Xianfang
Wei, Chenlong
Zheng, Pengcheng
Wei, Donghui
Fu, Zhenqian
Chi, Robin Yonggui
Huang, Wei
Keywords: Science::Chemistry
Issue Date: 2021
Source: Wang, G., Zhang, M., Guan, Y., Zhang, Y., Hong, X., Wei, C., Zheng, P., Wei, D., Fu, Z., Chi, R. Y. & Huang, W. (2021). Desymmetrization of cyclic 1,3-Diketones under N-Heterocyclic carbene organocatalysis: access to organofluorines with multiple stereogenic centers. Research, 2021, 9867915-.
Journal: Research
Abstract: Symmetric 1,3-diketones with fluorine or fluorinated substituents on the prochiral carbon remain to be established. Herein, we have developed a novel prochiral fluorinated oxindanyl 1,3-diketone and successfully applied these substrates in carbene-catalyzed asymmetric desymmetrization. Accordingly, a versatile strategy for asymmetric generation of organofluorines with fluorine or fluorinated methyl groups has been developed. Multiple stereogenic centers were selectively constructed with satisfactory outcomes. Structurally diverse enantioenriched organofluorines were generated with excellent results in terms of yields, diastereoselectivities, and enantioselectivities. Notably, exchanging fluorinated methyl groups to fluorine for this prochiral 1,3-diketones leads to switchable stereoselectivity. Mechanistic aspects and origin of stereoselectivity were studied by DFT calculations. Notably, some of the prepared organofluorines demonstrated competitive antibacterial activities.
ISSN: 2096-5168
DOI: 10.34133/2021/9867915
Schools: School of Physical and Mathematical Sciences 
Rights: © 2021 Guanjie Wang et al. Exclusive Licensee Science and Technology Review Publishing House. Distributed under a Creative Commons Attribution License (CC BY 4.0).
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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