A palladium catalyzed asymmetric desymmetrization approach to enantioenriched 1,3-disubstituted isoindolines

Dethe, Dattatraya H.; Kumar, Vimlesh; Shukla, Manmohan

doi:10.1039/d3sc03496h

Chem. Sci.

2023

DOI: 10.1039/d3sc03496h

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A palladium catalyzed asymmetric desymmetrization approach to enantioenriched 1,3-disubstituted isoindolines

Dattatraya H. Dethe,

Vimlesh Kumar,

Manmohan Shukla

Abstract: Herein, we report the first palladium/MPAA catalyzed enantioselective C–H activation/[4 + 1] annulation of diarylmethyltriflamide and olefins to construct chiral cis-1,3-disubstituted isoindoline derivatives.

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2024

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Cited by 7 publications

References 56 publications

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Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chen,

Xu,

Liu

et al. 2024

Angewandte Chemie

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Herein, multiple types of chiral Os(II) complexes have been designed to address the appealing yet challenging asymmetric C(sp3)‐H functionalization, among which the Os(II)/Salox species is found to be the most efficient for precise stereocontrol in realizing the asymmetric C(sp3)‐H amidation. As exemplified by the enantioenriched pyrrolidinone synthesis, such tailored Os(II)/Salox catalyst efficiently enables an intramolecular site‐/enantioselective C(sp3)‐H amidation in the γ‐position of dioxazolone substrates, in which benzyl, propargyl and allyl groups bearing various substituted forms are well compatible, affording the corresponding chiral γ‐lactam products with good er values (up to 99:1) and diverse functionality (> 35 examples). The unique performance advantage of the developed chiral Os(II)/Salox system in terms of the catalytic energy profile and the chiral induction has been further clarified by integrated experimental and computational studies.

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Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chen,

Xu,

Liu

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chen,

Xu,

Liu

et al. 2024

Angew Chem Int Ed

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Ru(II)‐Catalyzed C−H Alkylation of N‐Benzyltriflamide with Maleimides: Synthesis of o‐Succinimide Substituted Benzaldehydes

Dethe,

Kumar,

Datta

2024

Chemistry A European J

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A ruthenium‐catalyzed N‐benzyltriflamide assisted C‐H alkylation with maleimide followed by hydrolysis of in situ generated imine has been developed for the first time. This synthetic method results in the efficient synthesis of o‐succinimide derivatives of benzaldehydes. This reaction involves less expensive and mild reaction conditions and shows excellent site selectivity and good functional group compatibility.

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A palladium catalyzed asymmetric desymmetrization approach to enantioenriched 1,3-disubstituted isoindolines

Abstract: Herein, we report the first palladium/MPAA catalyzed enantioselective C–H activation/[4 + 1] annulation of diarylmethyltriflamide and olefins to construct chiral cis-1,3-disubstituted isoindoline derivatives.

Cited by 7 publications

References 56 publications

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Ru(II)‐Catalyzed C−H Alkylation of N‐Benzyltriflamide with Maleimides: Synthesis of o‐Succinimide Substituted Benzaldehydes

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A palladium catalyzed asymmetric desymmetrization approach to enantioenriched 1,3-disubstituted isoindolines

Abstract: Herein, we report the first palladium/MPAA catalyzed enantioselective C–H activation/[4 + 1] annulation of diarylmethyltriflamide and olefins to construct chiral cis-1,3-disubstituted isoindoline derivatives.

Cited by 7 publications

References 56 publications

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp3)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp3)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp3)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Ru(II)‐Catalyzed C−H Alkylation of N‐Benzyltriflamide with Maleimides: Synthesis of o‐Succinimide Substituted Benzaldehydes

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Product

Resources

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Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development

Chiral Osmium(II)/Salox Species Enabled Enantioselective γ‐C(sp³)−H Amidation: Integrated Experimental and Computational Validation For the Ligand Design and Reaction Development