Iron-catalyzed regio- and stereoselective substitution of gamma,delta-epoxy-alpha,beta-unsaturated esters and amides with Grignard reagents.
When gamma,delta-epoxy-alpha,beta-unsaturated esters or amides were treated with 2 equiv of Grignard reagents in the presence of 10-24 mol % FeCl(2), regio- and stereoselective substitution of the epoxide moiety with the Grignard reagent occurred to give exclusively delta-hydroxy-gamma-alkyl or aryl-alpha,beta-unsaturated esters or amides in good yields.
Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan.
Takeshi
T
Hata
Rie
R
Bannai
Mamoru
M
Otsuki
Hirokazu
H
Urabe
D000438:Alcohols / Q000737:chemistry; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000438:Alcohols; D000577:Amides; D004952:Esters; D007202:Indicators and Reagents; D007501:Iron