A preparation of haloalkylidene cyclopentanones

作者: Nicholas J. Cornwall , Shaun Linehan , Rex T. Weavers

DOI: 10.1016/S0040-4039(97)00503-0

关键词: Double bondKetoneOrganic chemistryStereoselectivityDegree (temperature)Chemistry

摘要: A radical-based 5-exo-dig cyclisation, initiated by addition of a trichloromethyl radical to an acyclic acetylenic ketone with appropriately positioned double bond, has been employed produce variety cyclic haloalkylidene cyclopentanones in moderate excellent yields and high degree stereoselectivity for the (E)-isomer.

参考文章(9)
Gerald Haaima, Mary-Jeanne Lynch, Anne Routledge, Rex T. Weavers, Alkylidene lactone synthesis Tetrahedron. ,vol. 47, pp. 5203- 5214 ,(1991) , 10.1016/S0040-4020(01)87132-5
Gerald Haaima, Mary-Jeanne Lynch, Anne Routledge, Rex T. Weavers, Synthesis of iodoalkylidene lactones from alkenes Tetrahedron. ,vol. 49, pp. 4229- 4252 ,(1993) , 10.1016/S0040-4020(01)85740-9
Gerald Haaima, Simon D. Mawson, Anne Routledge, Rex T. Weavers, Reaction of iodoalkylidene lactones with nucleophiles Tetrahedron. ,vol. 50, pp. 3557- 3570 ,(1994) , 10.1016/S0040-4020(01)87032-0
Bruno M. Giannetti, Bert Steffan, ]Wolfgang Steglich, Jutta Kupka, Timm Anke, Antibiotics from basidiomycetes. Part 24. Tetrahedron. ,vol. 42, pp. 3587- 3593 ,(1986) , 10.1016/S0040-4020(01)87325-7
Simon D. Mawson, Anne Routledge, Rex T. Weavers, IODOMETHYLENE LACTONE FORMATION AN IMPROVED SYNTHESIS Tetrahedron. ,vol. 51, pp. 4665- 4678 ,(1995) , 10.1016/0040-4020(95)00148-2
Thomas R. Hoye, Joseph A. Suriano, Dicobaltoctacarbonyl-mediated cyclizations of electron-deficient alkynones Journal of Organic Chemistry. ,vol. 58, pp. 1659- 1660 ,(1993) , 10.1021/JO00059A009
John M. Schwab, Daniel C. T. Lin, Stereochemical course of an enzyme-catalyzed allene−acetylene isomerization Journal of the American Chemical Society. ,vol. 107, pp. 6046- 6052 ,(1985) , 10.1021/JA00307A037
Zhi-Yu Liu, Wen Shi, Lian Zhang, A Practical Synthesis of a (±)-Sarkomycin Precursor Synthesis. ,vol. 1990, pp. 235- 236 ,(1990) , 10.1055/S-1990-26841