2009
DOI: 10.3998/ark.5550190.0010.615
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Samarium diiodide-induced reductive coupling of chiral nitrones prepared from D-isoascorbic acid with methyl acrylate

Abstract: 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 cyclizati… Show more

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Cited by 7 publications
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