Journal of Organic Chemistry p. 1856 - 1866 (1986)
Update date:2022-08-04
Topics: Functionalization Characterization Cyclization Cross-Coupling Reaction Purification and Isolation
Tanaka, Kazuhiko
Yoda, Hidemi
Isobe, Yutaka
Kaji, Aritsune
α-Methylene-γ-butyrolactones were prepared in high yields on treatment of N-monosubstituted 2-<(tributylstannyl)methyl>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-<(tributylstannyl)methyl>propenamides derived from optically active amines.Reaction of N-<(S)-α-(methoxymethyl)phenethyl>-2-<(tributylstannyl)methyl>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.
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