Convenient preparative method for synthesis of methyl (Z)-3-aryl-2-(carbobenzoxyamino)acrylates by Wittig-Horner reaction with the use of Et3N as a base

Article abstract of DOI:10.1007/BF00696717

The Wittig-Horner reaction of CbzNHCH(CO2Me)P(O)(OMe)2 (1) with ArCHO (2) in the presence of Et3N as a base affords methyl (Z)-3-aryl-2-(carbobenzoxyamino)acrylates (3) with high degrees of diastereoselectivity (Z)/(E) > 10:1.One recrystallization of the crude product is sufficient to obtain isomerically and chemically pure (Z)-3. - Keywords: α,β-dehydro-α-amino acids; Wittig-Horner reaction; diastereoselectivity; triethylamine; (Z)-3-aryl-2-(carbobenzoxyamino)acrylates; synthesis.