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Synthesis of Constrained C ‐Glycosyl Amino Acid Derivatives Involving 1,3‐Dipolar Cycloaddition of Cyclic Nitrone as Key Step
Author(s) -
Rouzier Florian,
Sillé Rosanne,
Montiège Ophélie,
Tessier Arnaud,
Pipelier Muriel,
Dujardin Gilles,
Martel Arnaud,
Nourry Arnaud,
Guillarme Stéphane
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001162
Subject(s) - nitrone , chemistry , cycloaddition , glycosyl , 1,3 dipolar cycloaddition , diastereomer , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
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.