Access to Enantioenriched Organosilanes from Enals and β‐Silyl Enones: Carbene Organocatalysis

Zhang, Yuxia; Huang, Jie; Guo, Yingying; Li, Lin; Fu, Zhenqian; Huang, Wei

doi:10.1002/ange.201800483

Cited by 18 publications

(4 citation statements)

References 122 publications

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“…[12] The carbene offered from the NHC 3 catalyzed and KOAc the formal [2 + 4] annulations in good yield and high stereoselectivity. In addition, Huang [13] and Tiwari [14] employed βsilyl enones and β-phosphonate-substituted enones to synthesize desired product respectively by NHC-catalyzed.…”

Section: The Nhc-enolate From Enalmentioning

confidence: 99%

NHC‐Activations on α‐, β‐, γ‐, and Beyond

Chen

Xia

et al. 2023

The Chemical Record

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Over the recent decades, due to the special electronic characteristics and diverse reactivities, N‐heterocyclic carbene (NHC) has received significant interest in organocatalyzed reactions. The formation of Breslow intermediates by NHC can convert into acyl anion equivalent, enolates, homoenolate, acyl azolium, and vinyl enolate etc., and the cycloaddition reactions of these species has attracted lots of attention. In this review, we focus on the summry of the development of NHC‐activation of carbonyl carbon (or imine carbon) in situ, α‐, β‐, γ‐, and beyond, and the cycloaddition reaction of these species.

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Section: The Nhc-enolate From Enalmentioning

confidence: 99%

NHC‐Activations on α‐, β‐, γ‐, and Beyond

Chen

Xia

et al. 2023

The Chemical Record

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“…Given the significant success of asymmetric N-heterocyclic carbene (NHC) catalysis [43][44][45][46][47][48][49][50][51][52] and privileged structural characters of prochiral 1,3-diketones, based on our ongoing interest in organocatalysis [53][54][55][56][57], we envisioned that a versatile method for the synthesis of enantioenriched organofluorines with multiple stereogenic centers might be established based on NHC-catalyzed asymmetric desymmetrization of novel prochiral fluorinated or fluoromethylated oxindolyl 1,3-ketones. Notably, asymmetric synthesis of spirocycle compounds has attracted a lot of synthetic attention [58][59][60][61].…”

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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“…The affinity of silicon towards carbon to form a carbon‐silicon (C–Si) bond is an interesting research problem since the fascinating chemistry was introduced by the landmark report of Friedel and Crafts . The formation of C–Si bond has been reached to the extensive levels of sophistication by the efforts of Grubbs and Stolz, Hiyama, Hartwig, Oestreich, Huang, and Arnold …”

Section: Introductionmentioning

confidence: 99%

Nickel‐Catalyzed Decarboxylative C–Si Bond Formation: A Regioselective Cross‐Coupling Between Trialkyl Silanes and α,β‐Unsaturated Carboxylic Acids

Allam

Azeez

Kandasamy

2019

Applied Organom Chemis

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This report presents the first example of nickel-catalyzed mild decarboxylative cross-coupling reaction for the regioselective formation of C-Si bond. An easily accessible and significantly stable Ni (dmg) 2 owes the role of key promoter. This reaction is highly functional group tolerant and offers α,β-unsaturated silanes in synthetically useful yields. The reaction gives access to the successful utilization of otherwise difficult trialkyl silanes as coupling partners and operates at a moderate temperature, which is beneficial to deal with highly volatile silanes.

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Access to Enantioenriched Organosilanes from Enals and β‐Silyl Enones: Carbene Organocatalysis

Cited by 18 publications

References 122 publications

NHC‐Activations on α‐, β‐, γ‐, and Beyond

NHC‐Activations on α‐, β‐, γ‐, and Beyond

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

Nickel‐Catalyzed Decarboxylative C–Si Bond Formation: A Regioselective Cross‐Coupling Between Trialkyl Silanes and α,β‐Unsaturated Carboxylic Acids

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