77407-49-9Relevant academic research and scientific papers
Asymmetric Synthesis of α-Methylene-γ-butyrolactones Using Chiral N-Monosubstituted 2-propenamides
Tanaka, Kazuhiko,Yoda, Hidemi,Isobe, Yutaka,Kaji, Aritsune
, p. 1856 - 1866 (2007/10/02)
α-Methylene-γ-butyrolactones were prepared in high yields on treatment of N-monosubstituted 2-propenamides with aldehydes in the presence of a Lewis acid followed by acidic hydrolysis of the resulting γ-hydroxy amides.Asymmetric synthesis of α-methylene-γ-butyrolactones was investigated by using a variety of chiral 2-propenamides derived from optically active amines.Reaction of N--2-propenamide or its antipode with aldehydes in the presence of 4 equiv of TiCl4 gave, after hydrolysis, α-methylene lactones in an enantiometric excess of as high as 80percent.Optically pure 3-methylene-2-pyrrolidinones were obtained in excellent yields by a one-pot sequence starting with the γ-hydroxy amides.
DIANION OF N-(o-METHOXYPHENYL)-2-METHYLPROPENAMIDE: A NEW REAGENT FOR THE CONVENIENT SYNTHESIS OF α-METHYLENE-γ-BUTYROLACTONES FROM CARBONYL COMPOUNDS
Tanaka, Kazuhiko,Nozaki, Yoshihito,Tamura, Norikazu,Tanikaga, Rikuhei,Kaji, Aritsune
, p. 1567 - 1568 (2007/10/02)
Dianion of N-(o-methoxyphenyl)-2-methylpropenamide was successfully generated on treatment of the amide with t-BuOK-BuLi at -78 degC in THF and utilized as the key reagent for the synthesis of γ-substituted α-methylene-γ-butyrolactones.
