Auxiliary‐Free Remote Dearomatizative Nitrenoid Transfer for Enantioselective Construction of Spirolactams

li, long; Zhu, Bo‐Han; Guo, Wenting; Sun, Qing; Qian, Peng‐Cheng; Ye, Long‐Wu

doi:10.1002/adsc.202101189

Adv Synth Catal

2021

DOI: 10.1002/adsc.202101189

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Auxiliary‐Free Remote Dearomatizative Nitrenoid Transfer for Enantioselective Construction of Spirolactams

long li

Bo‐Han Zhu

Wenting Guo

et al.

Abstract: An Ir‐catalyzed remote dearomatizative amidation for the enantioselective construction of chiral spirolactams in 70–93% yield with 81–96% ee was developed. This protocol represented a more atom‐economical approach to chiral spirolactams via Ir‐catalyzed nitrenoid transfer without the introduction of a traceless O‐silyl achiral auxiliary.

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Cited by 6 publications

References 62 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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Tandem Synthesis of 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones Based on Tf₂O-Promoted Activation of N-(2-Propyn-1-yl) Amides

Shan

Zheng

et al. 2022

J. Org. Chem.

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Structurally novel 2-azaspiro[4.5]deca-1,6,9-trien-8-ones were synthesized from N-(2-propyn-1-yl) amides and 1,3,5-trimethoxybenzenes by a tandem method consisting of a Tf2O-promoted amide activation and a TfOH-promoted Friedel–Crafts ipso-cyclization. The method offered the first example of using N-(2-propyn-1-yl) amides as substrates in both Tf2O-promoted secondary amide activation and the synthesis of azaspiro[4.5]deca-6,9-diene-8-ones.

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Auxiliary‐Free Remote Dearomatizative Nitrenoid Transfer for Enantioselective Construction of Spirolactams

Cited by 6 publications

References 62 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

Tandem Synthesis of 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones Based on Tf₂O-Promoted Activation of N-(2-Propyn-1-yl) Amides

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Auxiliary‐Free Remote Dearomatizative Nitrenoid Transfer for Enantioselective Construction of Spirolactams

Cited by 6 publications

References 62 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

Tandem Synthesis of 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones Based on Tf2O-Promoted Activation of N-(2-Propyn-1-yl) Amides

Contact Info

Product

Resources

About

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

Tandem Synthesis of 2-Azaspiro[4.5]deca-1,6,9-trien-8-ones Based on Tf₂O-Promoted Activation of N-(2-Propyn-1-yl) Amides