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
Revue
Org. Lett.
Volume
16
Pagination
1936–1939
ISSN
1523-7052
Soumis le 12 avril 2018