Tetrahedron Letters

Simple methods for the syntheses of (E)-4-and (E)-5-alkenoic acids by the SN2′ type reactions of γ-vinyl-γ-butyrolactone and δ-vinyl-δ-valerolactone with …

T Fujisawa, T Sato, M Kawashima, K Naruse…

Index: Fujisawa, Tamotsu; Sato, Toshio; Kawashima, Masatoshi; Naruse, Kouichi; Tamai, Kouichi Tetrahedron Letters, 1982 , vol. 23, # 35 p. 3583 - 3586

Full Text: HTML

Citation Number: 25

Abstract

Abstract γ-Vinyl-γ-butyrolactone and δ-vinylδ-valerolactone react regio-and stereoselectivity with Grignard reagents in the presence of a copper (I) catalyst or with diorganocuprates to afford (E)-4-and (E)-5-alkenoic acids, respectively, in high yields. Synthetic utility of the former reaction is demonstrated in the simple synthesis of (4E, 7Z)-4, 7-tridecadienyl acetate.

Related Articles:

Targeting Staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors

[Murray, Ewan J.; Crowley, Rebecca C.; Truman, Alex; Clarke, Simon R.; Cottam, James A.; Jadhav, Gopal P.; Steele, Victoria R.; O'Shea, Paul; Lindholm, Catharina; Cockayne, Alan; Chhabra, Siri Ram; Chan, Weng C.; Williams, Paul Journal of Medicinal Chemistry, 2014 , vol. 57, # 6 p. 2813 - 2819]

Regio-and stereoselective ring opening of. OMEGA.-alkenyllactones using organocopper reagents.

[Kawashima, Masatoshi; Sato, Toshio; Fujisawa, Tamotsu Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 3255 - 3264]

Stereochemically controlled synthesis of unsaturated acids via diphenylphosphinoyl (Ph 2 PO)-ketoacids

[Levin, Daniel; Warren, Stuart Tetrahedron Letters, 1985 , vol. 26, # 4 p. 505 - 508]

A simple, general distereoselective synthesis of 5-hydroxyalkylbutan-4-olides

[Jefford, Charles W.; Wang, Ying Journal of the Chemical Society, Chemical Communications, 1987 , # 20 p. 1513 - 1514]

A simple, general distereoselective synthesis of 5-hydroxyalkylbutan-4-olides

[Jefford, Charles W.; Wang, Ying Journal of the Chemical Society, Chemical Communications, 1987 , # 20 p. 1513 - 1514]

More Articles...