142602-53-7Relevant academic research and scientific papers
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
Tararov, V. I.,Savel'eva, T. F.,Belokon', Yu. N.
, p. 2124 - 2126 (1995)
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.
Diastereoselective formation of (Z)-didehydroamino acid esters
Schmidt,Griesser,Leitenberger,Lieberknecht,Mangold,Meyer,Riedl
, p. 487 - 490 (2007/10/02)
The rearrangement of (E)-didehydroamino acid derivatives to the corresponding Z-derivatives under acid or basic catalysis as well as under the influence of radicals has been investigated. The condensation of N-benzyloxycarbonyl or N-tert-butoxycarbonyl protected alkyl 2-amino-2-(dimethoxyphosphoryl)acetates with aldehydes or ketones in dichloromethane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene furnishes (Z)-didehydroamino acid ester derivatives diastereoselectively in excellent yields and with high purity.
