Nonracemizable isocyanoacetates for multicomponent reactions.
Chiral ortho esters of alpha-isocyano acids were synthesized from commercially available Cbz-protected alpha-amino acids. These compounds are stable toward racemization in the Ugi 4CC in contrast to known esters of alpha-isocyano acids. Applying them in Ugi 4CC with subsequent deprotection gives access to dipeptides with preserved configuration at the C-terminal amino acid.
Zhdanko
Alexander G
AG
Department of Chemistry, Moscow State University, Moscow, Russia.
Nenajdenko
Valentine G
VG
D000085:Acetates / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D004952:Esters