Catalytic asymmetric ring-opening of aminocyclopropanes with oxygen nucleophiles: access to chiral γ-amino acid derivatives

Luo, Ru-Lin; Wang, Xiao-Bing; Xie, Ming-Sheng; Guo, Hai-Ming

doi:10.1039/d3qo02036c

Cited by 3 publications

(1 citation statement)

References 56 publications

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“…Therefore, the development of asymmetric all-carbon-based IEDDA reactions with more electronically unbiased styrenes as dienophiles is still a worthy endeavor. Recently, we developed a chiral tridentate imidazolidine-pyrroloimidazolone pyridine (PyIPI) ligand and applied it in enantioselective dearomative (3 + 2) annulation, propargyl Claisen rearrangement, and ring-opening reactions . Herein, we report the asymmetric IEDDA reactions of 2-pyrones with styrenes and indenes to construct diverse bridged bicyclic lactones (Scheme d).…”

Section: Introductionmentioning

confidence: 99%

Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones with Styrenes and Indenes

Yu,

Chen,

Tian

et al. 2024

ACS Catal.

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With electronically unbiased styrenes and indenes as dienophiles, a highly enantioselective all-carbon-based inverseelectron-demand Diels−Alder reaction of electron-deficient 2-pyrones is reported. Using C 1 -symmetric imidazolidinepyrroloimidazolone pyridine as the tridentate ligand and Ni(OTf) 2 as the Lewis acid, diverse bridged bicyclic lactones were obtained in high yields (88−97% yields), diastereoselectivities (>95:5 dr), and enantioselectivities (90−99% ee). Cyclic enamine and 2,3-dihydrofuran were also suitable dienophiles. DFT calculations supported a concerted [4 + 2] cycloaddition mechanism for the Ni(II) complex-catalyzed reaction with high enantioselectivity caused by steric factors.

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Section: Introductionmentioning

confidence: 99%

Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones with Styrenes and Indenes

Yu,

Chen,

Tian

et al. 2024

ACS Catal.

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Imidazolidine‐Pyrroloimidazolone Pyridine‐Ni(acac)₂ Complex Catalyzed Asymmetric Darzens Reaction of Isatins with Phenacyl Chlorides: A Chiral Amplification Effect

Wang,

Wei,

et al. 2024

Adv Synth Catal

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With phenacyl chlorides as simple nucleophilic species, the asymmetric Darzens reaction of isatins using Ni(acac)2 as the Lewis acid and imidazolidine‐pyrroloimidazolone pyridine as the ligand is reported. In the presence of 1 mol% of catalyst, diverse spiro‐epoxyoxindoles with two new contiguous stereocenters were afforded in 82‐99% yields, >20:1 dr, and 91‐99% ee. Chiral spiro‐epoxyoxindoles could undergo ring‐opening reactions in further transformations. The developed method was applied to the derivatization of complex molecules including indomethacin, gemfibrozil, and febuxostat‐derived α‐chloroketones. A strong positive nonlinear effect was observed, which was caused by the precipitation of a less‐soluble racemic catalyst complex.

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Chemoselectivity Switch between Enantioselective [2,3]‐Wittig Rearrangement and Conia‐Ene‐Type Reactions of Propargyloxyoxindoles

Gao,

Yang,

et al. 2024

Chemistry A European J

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Despite the existence of three competing reactions for propargyloxyoxindoles, we report a chemoselectivity switch between enantioselective propargyl [2,3]‐Wittig rearrangement and Conia‐ene‐type reactions, with suppression of the [1,2]‐Wittig‐type rearrangement. Using C1‐symmetric imidazolidine‐pyrroloimidazolone pyridine as the ligand and Ni(acac)2 as the Lewis acid, diverse 3‐hydroxy 3‐substituted oxindoles containing allenyl groups were obtained in up to 98% yield and 99% ee via asymmetric propargyl [2,3]‐Wittig rearrangement. In the presence of AgOTf‐Duanphos, chiral spiro dihydrofuran oxindoles were given in up to 98% yield and 91% ee through a Conia‐ene‐type reaction.

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Catalytic asymmetric ring-opening of aminocyclopropanes with oxygen nucleophiles: access to chiral γ-amino acid derivatives

Abstract: Donor-acceptor aminocyclopropanes containing both amino and carboxyl groups underwent efficient catalytic asymmetric ring-opening reactions with diverse oxygen nucleophiles to afford chiral γ-oxygen substituted γ-aminobutyric acid derivatives in 60-96% yields and...

Cited by 3 publications

References 56 publications

Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones with Styrenes and Indenes

Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones with Styrenes and Indenes

Imidazolidine‐Pyrroloimidazolone Pyridine‐Ni(acac)₂ Complex Catalyzed Asymmetric Darzens Reaction of Isatins with Phenacyl Chlorides: A Chiral Amplification Effect

Chemoselectivity Switch between Enantioselective [2,3]‐Wittig Rearrangement and Conia‐Ene‐Type Reactions of Propargyloxyoxindoles

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Catalytic asymmetric ring-opening of aminocyclopropanes with oxygen nucleophiles: access to chiral γ-amino acid derivatives

Abstract: Donor-acceptor aminocyclopropanes containing both amino and carboxyl groups underwent efficient catalytic asymmetric ring-opening reactions with diverse oxygen nucleophiles to afford chiral γ-oxygen substituted γ-aminobutyric acid derivatives in 60-96% yields and...

Cited by 3 publications

References 56 publications

Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones with Styrenes and Indenes

Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Diels–Alder Reaction of 2-Pyrones with Styrenes and Indenes

Imidazolidine‐Pyrroloimidazolone Pyridine‐Ni(acac)2 Complex Catalyzed Asymmetric Darzens Reaction of Isatins with Phenacyl Chlorides: A Chiral Amplification Effect

Chemoselectivity Switch between Enantioselective [2,3]‐Wittig Rearrangement and Conia‐Ene‐Type Reactions of Propargyloxyoxindoles

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Imidazolidine‐Pyrroloimidazolone Pyridine‐Ni(acac)₂ Complex Catalyzed Asymmetric Darzens Reaction of Isatins with Phenacyl Chlorides: A Chiral Amplification Effect