Desymmetrization of Cyclic 1,3-Diketones Under -Heterocyclic Carbene Organocatalysis: Access to Organofluorines with Multiple Stereogenic Centers

Overview

Journal Research (Wash D C)

Specialty Biology

Date 2021 Sep 22

PMID 34549186

Citations 6

Authors

Guanjie Wang

Min Zhang

Yezhi Guan

Ye Zhang

Xianfang Hong

Chenlong Wei

Pengcheng Zheng

Donghui Wei

Zhenqian Fu

Yonggui Robin Chi

Wei Huang

Affiliations

Soon will be listed here.

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.

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