587840-66-2Relevant academic research and scientific papers
Preparation of protected syn-α,β-dialkyl β-amino acids that contain polar side chain functionality
Langenhan, Joseph M.,Gellman, Samuel H.
, p. 6440 - 6443 (2007/10/03)
We report the synthesis of syn-α,β-dialkyl β-amino acid derivatives suitably protected for solid-phase synthesis that give rise to residues containing positively charged lysine-like side chains. These amino acids, as well as synα,β-dialkyl β-amino acids that contain diverse hydrophobic side chains, are prepared in good de and ee. The key step in this route involves Davies's protocol for the conjugate addition of a chiral lithium amide to α,β-unsaturated tertbutyl esters (Davies, S. G.; Ichihara, 0.; Walters, I. A. S. J. Chem. Soc., Perkin Trans. 1 1994, 9, 1141). syn-α,β-Dialkyl β-amino acids are interesting building blocks because of their sheet-forming propensity and because of their presence in bioactive compounds.
