Asymmetric desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones using transition metal catalysis

Shu, Tao; Cossy, Janine

doi:10.1039/d0cs00666a

Cited by 81 publications

(19 citation statements)

References 23 publications

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“…varied desymmetric conjugate addition and cascade processes, which can construct fused cyclohexanones and cyclopentenones with high enantioselectivities. Achiral cyclohexadienones are one typical class of prochiral enones that are easily prepared from oxidation of parasubstituted phenols and have been widely utilized for desymmetrization [37,38].…”

Section: Desymmetrization Of Prochiral Ketones and Diketonesmentioning

confidence: 99%

Recent advances towards organocatalytic enantioselective desymmetrizing reactions

Zhai

et al. 2022

Trends in Chemistry

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Section: Desymmetrization Of Prochiral Ketones and Diketonesmentioning

confidence: 99%

Recent advances towards organocatalytic enantioselective desymmetrizing reactions

Zhai

et al. 2022

Trends in Chemistry

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“…Lithium‐ion batteries (LIBs) have taken a dominant position in the fields of portable electronic devices and electric vehicles since the 1990s, thanks to their high energy density, little memory effect, and long cycle life. [ 1 ] Despite the prosperity of various energy storage devices such as sodium‐ion batteries, [ 2,3 ] potassium‐ion batteries, [ 4 ] dual‐ion batteries, [ 5,6 ] etc. LIBs are still the favorite in terms of energy density and cycling stability.…”

Section: Introductionmentioning

confidence: 99%

A Vanadium‐Based Fluoroxide Cathode Material for Lithium‐Ion Storage with High Energy Density

et al. 2022

Advanced Sustainable Systems

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High‐performance lithium‐ion batteries (LIBs) are required for the rising energy storage demand, while their development depends mainly on cathode materials. Vanadium‐based compounds are considered to be promising due to the feasibility of multielectron reactions arising from the rich valence states of vanadium (+2 to +5). Herein, for the first time the electrochemical properties of a vanadium‐based fluoroxide, β‐KVOF3, as a cathode for LIBs, are reported. After optimization, a reversible capacity as high as 274 mAh g−1, a stable 300 cycles lifetime, and an energy density comparable to LiFePO4 (650 vs 550 Wh kg−1) are achieved. Experiments and simulation study of reaction mechanism illustrate that such performance originates from the reversible V3+/V5+ redox reaction, high structural stability of β‐KVOF3, and the pseudocapacitive process during charging and discharging. This study reveals that β‐KVOF3 is a promising cathode for Li‐ion storage and provides a new design idea for developing high‐performance LIBs cathode materials.

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“…Asymmetric desymmetrization represents one of the most facile and efficient methods for the generation of enantioenriched organic compounds, especially with multiple stereogenic centers, from meso or prochiral raw materials [1][2][3][4]. In this area, catalytic desymmetrization of prochiral 1,3-diketones has been investigated widely, including asymmetric reduction, intramolecular adol-type reactions, and others [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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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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Asymmetric desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones using transition metal catalysis

Abstract: This review is covering the recent development of catalytic asymmetric domino reactions for the desymmetrization of alkene-, alkyne- and allene-tethered cyclohexadienones using transition metals and chiral ligands.

Cited by 81 publications

References 23 publications

Recent advances towards organocatalytic enantioselective desymmetrizing reactions

Recent advances towards organocatalytic enantioselective desymmetrizing reactions

A Vanadium‐Based Fluoroxide Cathode Material for Lithium‐Ion Storage with High Energy Density

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

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