A novel synthesis of α-methylene-γ-butyrolactones

H Saimoto, K Nishio, H Yamamoto, M Shinoda…

Index: Saimoto; Nishio; Yamamoto; Shinoda; Hiyama; Nozaki Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 10 p. 3093 - 3098

Full Text: HTML

Citation Number: 14

Abstract

A new method is reported for constructing α-methylene-γ-butyrolactone moiety under neutral, anhydrous conditions. Olefin–dibromocarbene adducts were transformed into methyl 1-(dimethylaminomethyl) cyclopropanecarboxylates (3). Treatment of 3 with trimethylsilyl iodide followed by thermolytic distillation of the crude products gave α- methylene-γ-butyrolactones with high regio-and stereo selectivity.

Related Articles:

Palladium-catalyzed cyclocarbonylation of acetylenic alcohols to methylene lactones. Scope and synthesis of appropriate substrates

[Murray,T.F.; Samsel,E.G.; Varma,V. Journal of the American Chemical Society, 1981 , vol. 103, p. 7520]

4-(Dimethylamino) pyridine as a catalyst for the lactonization of 4-hydroxy-2-methylenebutanoate esters

[Nicponski, Daniel R. Tetrahedron Letters, 2014 , vol. 55, # 13 p. 2075 - 2077]

A new method using 2-chloro-4, 6-dimethoxy-1, 3, 5-triazine for facile elimination of dimethylamino group in Eschenmoser's methylenation for synthesis of α, β- …

[Tetrahedron Letters, , vol. 54, # 13 p. 1758 - 1760]

Synthesis of unsaturated butyrolactones by palladium catalyzed intramolecular carboalkoxylation of homoallylic chloroformates

[Henin, Francoise; Pete, Jean-Pierre Tetrahedron Letters, 1983 , vol. 24, # 43 p. 4687 - 4690]

New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (±)-cinnamolide and (±)-methylenolactocin

[Forbes, Judith E.; Saicic, Radomir N.; Zard, Samir Z. Tetrahedron, 1999 , vol. 55, # 12 p. 3791 - 3802]

More Articles...