Synthesis of Perfluoroalkyl-Substituted Vinylcyclopropanes by Way of Enhanced Neighboring Group Participation
作者： Christopher B. Kelly , Michael A. Mercadante , Emma R. Carnaghan , Matthew J. Doherty , Diana C. Fager
关键词:
摘要: A simple, high yielding, two-step, one-pot protocol for the preparation of trifluoromethyl-substituted vinylcyclopropanes from α-CF3 homoallyl alcohols is disclosed. Destabilization cationic intermediate by electron-withdrawing CF3 group greatly enhances neighboring participation alkene, allowing ring closure to predominate. The reaction can be extended difluoromethyl and pentafluoroethyl group, enabling a diverse array fluoroalkyl-substituted vinylcyclopropanes.
sci-hub.se 参考文章(39)
Jacques Salaün, Cyclopropane Derivatives and their Diverse Biological Activities Topics in Current Chemistry. ,vol. 207, pp. 1- 67 ,(2000) , 10.1007/3-540-48255-5_1
Helmut Vorbrüggen, On Novel Fluorine Reagents in Preparative Organic Chemistry Helvetica Chimica Acta. ,vol. 94, pp. 947- 965 ,(2011) , 10.1002/HLCA.201100039
Matthias Scholl, Sheng Ding, Choon Woo Lee, Robert H. Grubbs, Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Organic Letters. ,vol. 1, pp. 953- 956 ,(1999) , 10.1021/OL990909Q
Derek W. Nelson, Neil J. O'Reilly, Jon Speier, Paul G. Gassman, Synthesis and Solvolysis of 7-(Perfluoroalkyl)-7-bicyclo[2.2.1]heptyl Derivatives Journal of Organic Chemistry. ,vol. 59, pp. 8157- 8171 ,(1994) , 10.1021/JO00105A037
Xavier Creary, Benjamin D. O'Donnel, Marie Vervaeke, Homoallyl-cyclopropylcarbinyl cation manifold. Trimethylsilyl versus aryl stabilization. Journal of Organic Chemistry. ,vol. 72, pp. 3360- 3368 ,(2007) , 10.1021/JO062668N
Paul G. Gassman, Thomas T. Tidwell, Electron-deficient carbocations Accounts of Chemical Research. ,vol. 16, pp. 279- 285 ,(1983) , 10.1021/AR00092A003
V. J. Shiner, Mark W. Ensinger, Randy D. Rutkowske, .gamma.-Silicon stabilization of carbonium ions in solvolysis. 2. Solvolysis of 4-(trimethylsilyl)-2-butyl p-bromobenzenesulfonates Journal of the American Chemical Society. ,vol. 109, pp. 7199- 7205 ,(1987) , 10.1021/JA00237A027
Arthur Greenberg, Joel F. Liebman, Deborah Van Vechten, On the nature of the perfluoroalkyl (Rf) effect Tetrahedron. ,vol. 36, pp. 1161- 1166 ,(1980) , 10.1016/0040-4020(80)87012-8
Nicholas A. Meanwell, Synopsis of some recent tactical application of bioisosteres in drug design. Journal of Medicinal Chemistry. ,vol. 54, pp. 2529- 2591 ,(2011) , 10.1021/JM1013693
Ronald K. Crossland, Kenneth L. Servis, Facile synthesis of methanesulfonate esters Journal of Organic Chemistry. ,vol. 35, pp. 3195- 3196 ,(1970) , 10.1021/JO00834A087