351340-72-2Relevant academic research and scientific papers
A β-lactam-based stereoselective access to β,γ-dihydroxy α-amino acid-derived peptides with either α,β-like or unlike configurations
Palomo,Oiarbide,Landa,Esnal,Linden
, p. 4180 - 4186 (2007/10/03)
A concise access to α,β-dihydroxy α-amino acid-derived N-carboxy anhydrides (NCAs) with either like or unlike relative configuration is described. The key steps of the synthetic route are the preparation of the nonracemic 4-alkenyl β-lactams, through either Homer-type olefination of a common 4-formyl β-lactam or the Corey-Winter alkene synthesis applied to 4-dihydroxyalkyl β-lactams, followed by the Sharpless AD reaction, and a subsequent ring expansion of the corresponding 4-substituted 3-hydroxy β-lactams promoted by TEMPO. The opening of thus-prepared NCAs upon treatment with different O- and N-nucleophiles, including α-amino esters which lead to peptides, has also been studied under various reaction conditions.
