Asymmetric Synthesis of α,α-Disubstituted Amino Acids by Cycloaddition of (E)-Ketonitrones with Vinyl Ethers.
Original acyclic (E)-alpha,alpha-dialkylketonitrones bearing a chiral auxiliary on their nitrogen atom were synthesized and successfully employed for the asym. synthesis of alpha,alpha-disubstituted amino acids using regio- and stereocontrolled 1,3-dipolar cycloaddn. reactions with vinyl ethers. N-Glycosyl chiral auxiliaries were found to provide excellent exo- and π-facial stereocontrol. The obtained enantiopure cycloadducts were selectively transformed into functional alpha,alpha-disubstituted amino acids and related beta-peptides through the highly regioselective opening of an intermediate quaternary anhydride.
Références
- Titre
- Asymmetric Synthesis of α,α-Disubstituted Amino Acids by Cycloaddition of (E)-Ketonitrones with Vinyl Ethers.
- Type de publication
- Article de revue
- Année de publication
- 2014
- Auteurs
- Zhang, Xiaofei, Cividino Pascale, Poisson Jean-François, Shpak-Kraievskyi Pavlo, Laurent Mathieu Y., Martel Arnaud, Dujardin Gilles, and Py Sandrine
- Revue
- Org. Lett.
- Volume
- 16
- Pagination
- 1936–1939
- ISSN
- 1523-7052
Soumis le 12 avril 2018