Iron(<scp>iii</scp>)/quinoxaline-derived N,N-ligand catalyzed oxygen transfer reaction of <i>N</i>-vinyl nitrones through selective 4π-electrocyclization and N–O bond cleavage

Lu, Yan-Jiao; Lu, Feng-Lan; Zhang, Jin-Qi; Chen, Chun-Hua; Liang, Cui; Ma, Xiao-Pan; Mo, Dong-Liang

doi:10.1039/d3qo01999c

Org. Chem. Front.

2024

DOI: 10.1039/d3qo01999c

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Iron(iii)/quinoxaline-derived N,N-ligand catalyzed oxygen transfer reaction of N-vinyl nitrones through selective 4π-electrocyclization and N–O bond cleavage

Yan-Jiao Lu,

Feng-Lan Lu,

Jin-Qi Zhang

et al.

Abstract: We describe an iron(iii)/quinoxaline-derived N,N-ligand promoted O-transfer reaction of N-vinyl nitrones through selective O-4π-electrocyclization and N–O bond cleavage to prepare a variety of 2,5-dihydrooxazoles in good yields.

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Cited by 3 publications

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Asymmetric [3+3] Cycloaddition of N‐Vinyl Oxindole Nitrones with 2‐Indolylmethanols to Prepare Spirooxindole[1,2]oxazines

Zou,

Wu,

Zhong

et al. 2024

Adv Synth Catal

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We describe a chiral phosphoric acid (CPA) catalyzed asymmetric [3+3] cycloaddition of N‐viny oxindole nitrones with 2‐indolylmethanols to prepare various spirooxindole[1,2]oxazines in 43‐93% yields and 88:12‐97:3 enantiomeric ratios. Experimental results revealed that the addition of hexafluoroisopropanol (HFIP) played important roles to help CPA control the reaction reactivity and enantioselectivity. The present method features the construction of tetrasubstituted chiral carbon stereocenter and the example of N‐vinyl nitrones in asymmetric [3+3] cycloaddition.

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Asymmetric [3+3] Cycloaddition of N‐Vinyl Oxindole Nitrones with 2‐Indolylmethanols to Prepare Spirooxindole[1,2]oxazines

Zou,

Wu,

Zhong

et al. 2024

Adv Synth Catal

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Yb(OTf)₃‐Catalyzed Asymmetric [3+3] Cycloaddition of N‐Vinyl Nitrones with Activated Cyclopropanes to Prepare 1,2‐Oxazines

Wu,

Leng,

Chen

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryWe described a Yb(OTf)3 combined with Pybox ligand catalyzed asymmetric [3+3] cycloaddition of N‐vinyl cinnamaldehyde nitrones with activated cyclopropanes to prepare various functionalized 1,2‐oxazines in 24%—95% yields and 22%—96% ee. Experimental results revealed that the reaction underwent a domino [3+3] cycloaddition, dealkenylation, and aza‐1,4‐addition in three steps. The chiral 1,2‐oxazine could be obtained in gram scales and easily converted into various 1,2‐oxazine scaffolds. The present method features broad substrate scope, good functional group compatibility, three‐component domino reaction, and asymmetric [3+3] cycloaddition of N‐vinyl nitrones with activated cyclopropanes.

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Iron(III) and BF₃·OEt₂-Promoted O-Transfer Reaction of N-Aryl-α,β-Unsaturated Nitrones to Prepare Difluoroboron β-Ketoiminates

Li,

Liao,

Ding

et al. 2024

Org. Lett.

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We described an iron(III) and BF 3 •OEt 2 -promoted oxygen transfer reaction of N-aryl-α,β-unsaturated nitrones to prepare various N,O-difluoroboron β-ketoiminates in good yields ranging from 24% to 87%. Control experiments revealed that the enaminone was the vital intermediate for the formation of N,Odifluoroboron β-ketoiminates, and iron(III) combined with BF 3 • OEt 2 played as cocatalyst to promote the oxygen transfer reaction through intramolecular cyclization and N−O bond cleavage. More importantly, an estrone-derived N,O-difluoroboron β-ketoiminate was easily prepared in 40% yield from estrone in four steps.

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Iron(iii)/quinoxaline-derived N,N-ligand catalyzed oxygen transfer reaction of N-vinyl nitrones through selective 4π-electrocyclization and N–O bond cleavage

Abstract: We describe an iron(iii)/quinoxaline-derived N,N-ligand promoted O-transfer reaction of N-vinyl nitrones through selective O-4π-electrocyclization and N–O bond cleavage to prepare a variety of 2,5-dihydrooxazoles in good yields.

Cited by 3 publications

References 39 publications

Asymmetric [3+3] Cycloaddition of N‐Vinyl Oxindole Nitrones with 2‐Indolylmethanols to Prepare Spirooxindole[1,2]oxazines

Asymmetric [3+3] Cycloaddition of N‐Vinyl Oxindole Nitrones with 2‐Indolylmethanols to Prepare Spirooxindole[1,2]oxazines

Yb(OTf)₃‐Catalyzed Asymmetric [3+3] Cycloaddition of N‐Vinyl Nitrones with Activated Cyclopropanes to Prepare 1,2‐Oxazines

Iron(III) and BF₃·OEt₂-Promoted O-Transfer Reaction of N-Aryl-α,β-Unsaturated Nitrones to Prepare Difluoroboron β-Ketoiminates

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Iron(iii)/quinoxaline-derived N,N-ligand catalyzed oxygen transfer reaction of N-vinyl nitrones through selective 4π-electrocyclization and N–O bond cleavage

Abstract: We describe an iron(iii)/quinoxaline-derived N,N-ligand promoted O-transfer reaction of N-vinyl nitrones through selective O-4π-electrocyclization and N–O bond cleavage to prepare a variety of 2,5-dihydrooxazoles in good yields.

Cited by 3 publications

References 39 publications

Asymmetric [3+3] Cycloaddition of N‐Vinyl Oxindole Nitrones with 2‐Indolylmethanols to Prepare Spirooxindole[1,2]oxazines

Asymmetric [3+3] Cycloaddition of N‐Vinyl Oxindole Nitrones with 2‐Indolylmethanols to Prepare Spirooxindole[1,2]oxazines

Yb(OTf)3‐Catalyzed Asymmetric [3+3] Cycloaddition of N‐Vinyl Nitrones with Activated Cyclopropanes to Prepare 1,2‐Oxazines

Iron(III) and BF3·OEt2-Promoted O-Transfer Reaction of N-Aryl-α,β-Unsaturated Nitrones to Prepare Difluoroboron β-Ketoiminates

Contact Info

Product

Resources

About

Yb(OTf)₃‐Catalyzed Asymmetric [3+3] Cycloaddition of N‐Vinyl Nitrones with Activated Cyclopropanes to Prepare 1,2‐Oxazines

Iron(III) and BF₃·OEt₂-Promoted O-Transfer Reaction of N-Aryl-α,β-Unsaturated Nitrones to Prepare Difluoroboron β-Ketoiminates