Synthesis of Constrained C‐Glycosyl Amino Acid Derivatives Involving 1,3‐Dipolar Cycloaddition of Cyclic Nitrone as Key Step

An efficient two‐step strategy for the synthesis of constrained C‐glycosyl amino acid derivatives from C‐vinylglycosides involving a 1,3‐dipolar cycloaddition using l‐(–)‐menthone‐derived nitrone as the key step is described. After optimization of 1,3‐dipolar cycloaddition conditions, various C‐viny...

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Published inEuropean journal of organic chemistry Vol. 2020; no. 43; pp. 6749 - 6757
Main Authors Rouzier, Florian, Sillé, Rosanne, Montiège, Ophélie, Tessier, Arnaud, Pipelier, Muriel, Dujardin, Gilles, Martel, Arnaud, Nourry, Arnaud, Guillarme, Stéphane
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 22.11.2020
Wiley Subscription Services, Inc
Wiley-VCH Verlag
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ISSN1434-193X
1099-0690
DOI10.1002/ejoc.202001162

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Summary:An efficient two‐step strategy for the synthesis of constrained C‐glycosyl amino acid derivatives from C‐vinylglycosides involving a 1,3‐dipolar cycloaddition using l‐(–)‐menthone‐derived nitrone as the key step is described. After optimization of 1,3‐dipolar cycloaddition conditions, various C‐vinylglycosides were tested leading exclusively to one diastereoisomer of the corresponding cycloadduct in good to excellent yields. The total facial selectivity observed was also studied by DFT calculations. Original conformationally restricted C‐glycosyl amino acid derivatives (8 examples) were isolated after simple cleavage of the chiral auxiliary. Original conformationally restricted C‐glycosyl amino acid derivatives in different series have been isolated following a two‐step strategy involving 1,3‐dipolar cycloaddition between l‐(–)‐menthone‐derived nitrone and C‐vinylglycosides as the key step. The cycloaddition reaction was highly regio‐ and stereoselective leading to corresponding cycloadducts in high yield. Simple cleavage of the chiral auxiliary allows preparing C‐glycosyl amino acid analogs.
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ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202001162