405095-67-2Relevant academic research and scientific papers
Stereoselective synthesis of a set of two functionalized (E)-alkene dipeptide isosteres of L-amino acid-L-Glu and L-amino acid-D-Glu
Oishi, Shinya,Tamamura, Hirokazu,Yamashita, Masaki,Odagaki, Yoshihiko,Hamanaka, Nobuyuki,Otaka, Akira,Fujii, Nobutaka
, p. 2445 - 2451 (2007/10/03)
The stereoselective synthesis of a set of two functionalized (E)-alkene dipeptide isosteres of L-amino acid-L-Glu and L-amino acid-D-Glu was carried out. The treatment of N-arylsulfonyl-γ,δ-cis- or -trans-γ,δ-epimino (E)-α,β-enoates with HCl-1,4-dioxane afforded regio- and stereo-selective ring-opened products. The ring-opening reaction provided a useful method for the stereoselective synthesis of a set of diastereomeric (L-Xaa, L-Glu)-type and (L-Xaa, D-Glu)-type (E)-alkene dipeptide isosteres (EADI) from a single substrate of γ,δ-epimino (E)-α,β-enoate using organozinc-copper reagents.
