1257874-86-4Relevant articles and documents
Ugi and Passerini reactions of biocatalytically derived chiral aldehydes: Application to the synthesis of bicyclic pyrrolidines and of antiviral agent telaprevir
Moni, Lisa,Banfi, Luca,Basso, Andrea,Carcone, Luca,Rasparini, Marcello,Riva, Renata
, p. 3411 - 3428 (2015)
Lipase mediated desymmetrization of a meso-diol (1,2-cyclopentanedimethanol) allows the synthesis of both enantiomers of some chiral aldehydes, whose behavior in Passerini and Ugi reactions has been explored. Exploiting these two complementary multicomponent reactions and coupling them with a subsequent cyclization process, we observed that 6 out of all 8 possible stereoisomers of peptidomimetic pyrrolidines can be obtained in good yields. The potential of these protocols has been proved by the development of a new efficient synthesis of antiviral drug telaprevir.