302571-80-8Relevant articles and documents
Iron-Catalyzed Regio- And Stereoselective Substitution of γ,δ-Epoxy-α,β-unsaturated Esters and Amides with Grignard Reagents
Hata, Takeshi,Bannai, Rie,Otsuki, Mamoru,Urabe, Hirokazu
experimental part, p. 1012 - 1014 (2010/06/15)
Chemical Equetion Presentation When γ,δ-epoxy-α,β- unsaturated esters or amides were treated with 2 equiv of Grignard reagents in the presence of 10-24 mol % FeCl2, regio- and stereoselective substitution of the epoxide moiety with the Grignard reagent occurred to give exclusively δ-hydroxy-γ-alkyl or aryl-α,β-unsaturated esters or amides in good yields.
Sequential reactions promoted by manganese: Completely stereoselective synthesis of (E)-α,β-unsaturated amides, ketones, aldehydes, and carboxylic acids
Concellon, Jose M.,Rodriguez-Solla, Humberto,Diaz, Pamela
, p. 7974 - 7979 (2008/02/13)
(Chemical Equation Presented) A complete E-selective synthesis of α,β-unsaturated amides through a sequential reaction of a range of dichloroamides with a variety of aldehydes promoted by Rieke manganese (Mn*) is reported. A mechanism based on a sequential aldol-type reaction and a completely stereoselective β-elimination is proposed to explain these results. The unsaturated amides obtained are readily and efficiently transformed into α,β-unsaturated ketones, aldehydes, or carboxylic acids without loss of the diastereoisomeric purity of the C-C double bond.
Synthesis of (E)-α,β-unsaturated amides with high selectivity by using samarium diiodide
Concellon, Jose M.,Perez-Andres, Juan A.,Rodriguez-Solla, Humberto
, p. 3062 - 3068 (2007/10/03)
Stereoselective β-elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield α,β-unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds 1 are easily prepared by reaction of the c
