1582763-07-2Relevant academic research and scientific papers
Asymmetric synthesis of α,α-disubstituted amino acids by cycloaddition of (E)-ketonitrones with vinyl ethers
Zhang, Xiaofei,Cividino, Pascale,Poisson, Jean-Francois,Shpak-Kraievskyi, Pavlo,Laurent, Mathieu Y.,Martel, Arnaud,Dujardin, Gilles,Py, Sandrine
, p. 1936 - 1939 (2014)
Original acyclic (E)-α,α-dialkylketonitrones bearing a chiral auxiliary on their nitrogen atom were synthesized and successfully employed for the asymmetric synthesis of α,α-disubstituted amino acids using regio- and stereocontrolled 1,3-dipolar cycloaddition 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 α,α-disubstituted amino acids and related β-peptides through the highly regioselective opening of an intermediate quaternary anhydride.
