Synthesis of N-Benzyl Nitrones

Dondoni, Alessandro; Franco, Santiago; Junquera, F.; Merchán, F. L.; Merino, Pedro; Tejero, Tomás

doi:10.1080/00397919408010565

Cited by 148 publications

(80 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Furan-derived nitrones were prepared according to our method [6] from furfural and the corresponding benzyl hydroxylamine. In both cases only the Z-isomer was detected, the configuration being assigned on the basis of NOE experiments (a 10-12% enhancement was observed in the difference spectra upon irradiation of the azomethine proton of the nitrone and the benzylic protons.…”

Section: Resultsmentioning

confidence: 99%

1,3-Dipolar Cycloadditions of N-Benzyl Furfuryl Nitrones with Electron-rich Alkenes

et al. 2000

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

1,3-Dipolar Cycloadditions of N-Benzyl Furfuryl Nitrones with Electron-rich Alkenes

et al. 2000

View full text Add to dashboard Cite

show abstract

“…Whereas the synthesis of D-erythrose derived nitrone 13 starting from D-isoascorbic acid has been reported in the literature, 10 In contrast, when D-erythrose derived nitrone 14 possessing a free hydroxyl group was treated with three equivalents of SmI 2 and eight equivalents of H 2 O in THF at -78° C over two hours with methyl acrylate, the expected γ-N-hydroxylamino ester 21 was obtained in low 5% yield along with dimethyl adipate (70%) and substantial amounts of unreacted nitrone 14 (44%, Scheme 6). On the other hand the reaction is completely diastereoselective (>95:5) within the limits of NMR analysis of the crude product.…”

Section: Resultsmentioning

confidence: 99%

Samarium diiodide-induced reductive coupling of chiral nitrones prepared from D-isoascorbic acid with methyl acrylate

Rehák¹,

Fišera

Prónayová

2009

Arkivoc

View full text Add to dashboard Cite

Chiral nitrones 13-15 prepared from D-isoascorbic acid were found to effectively undergo an SmI 2 -mediated radical addition to methyl acrylate affording γ-N-hydroxylamino esters 19-22 with high diastereomeric control. The unsubstituted nitrone 14 afforded in the SmI 2 -induced coupling with methyl acrylate the γ-N-hydroxylamino ester 21 as minor product. The pyrrolidinones 23-25 were prepared in a single step from 19 and 22 involving N-O bond cleavage with Zn/AcOH or SmI 2 and subsequent spontaneous cyclization.

show abstract

“…2i, 8 When treated with samarium diiodide 9 (3 equiv.) at -78 °C, nitrone 7 was reduced to an α-amino radical species, that was trapped in situ with methyl acrylate (2, 1.4 equiv.).…”

Section: Methodsmentioning

confidence: 99%

Samarium diiodide-induced reductive coupling of chiral nitrones with methyl acrylate

Rehák¹,

Fišera²,

Kožı́šek³

et al. 2007

Arkivoc

View full text Add to dashboard Cite

D-Lyxose derived nitrone 7 was found to effectively undergo an SmI 2 -mediated radical addition to methyl acrylate affording γ-N-hydroxylamino ester 8 with high diastereomeric control. The pyrrolidinone 9 was prepared in a single step from 8 involving N-O bond cleavage with Zn/AcOH and subsequent spontaneous cyclization. D-Xylose derived nitrone 10 afforded in the SmI 2 -induced coupling with methyl acrylate the γ-N-hydroxylamino ester 11 as minor product. The major product the nitrone 12 is formed by unusual reductive deoxygenation of the starting nitrone.

show abstract

Synthesis of N-Benzyl Nitrones

Cited by 148 publications

References 37 publications

1,3-Dipolar Cycloadditions of N-Benzyl Furfuryl Nitrones with Electron-rich Alkenes

1,3-Dipolar Cycloadditions of N-Benzyl Furfuryl Nitrones with Electron-rich Alkenes

Samarium diiodide-induced reductive coupling of chiral nitrones prepared from D-isoascorbic acid with methyl acrylate

Samarium diiodide-induced reductive coupling of chiral nitrones with methyl acrylate

Contact Info

Product

Resources

About