Remarkable selectivity in the cyclopropanation reactions catalysed by an halogenated iron meso-tetraphenylporphyrin
作者： Pietro Tagliatesta , Alessandra Pastorini
DOI: 10.1016/S1381-1169(02)00698-2
关键词:
摘要: Abstract Iron(II) meso -tetra(2′,6′-dichlorophenyl)porphyrin, Fe II (TDCPP) catalyses the cyclopropanation of styrenes by ethyldiazoacetate with high yields and remarkable anti selectivities. The reaction mechanism is discussed compared that for rhodium catalysts. Some evidences presence a radical intermediate in iron catalysed reactions are also discussed.
elsevier.com
sci-hub.se 参考文章(12)
Christopher G. Hamaker, Gholam A. Mirafzal, L. Keith Woo, Catalytic Cyclopropanation with Iron(II) Complexes Organometallics. ,vol. 20, pp. 5171- 5176 ,(2001) , 10.1021/OM010513U
Jennifer Robbins Wolf, Christopher G. Hamaker, Jean-Pierre Djukic, Thomas Kodadek, L. Keith Woo, Shape and stereoselective cyclopropanation of alkenes catalyzed by iron porphyrins. Journal of the American Chemical Society. ,vol. 117, pp. 9194- 9199 ,(1995) , 10.1021/JA00141A011
Pietro Tagliatesta, Alessandra Pastorini, Electronic and steric effects on the stereoselectivity of cyclopropanation reactions catalysed by rhodium meso-tetraphenylporphyrins Journal of Molecular Catalysis A-chemical. ,vol. 185, pp. 127- 133 ,(2002) , 10.1016/S1381-1169(02)00080-8
Christopher G. Hamaker, Jean-Pierre Djukic, Daniel A. Smith, L. Keith Woo, Mechanism of Cyclopropanation Reactions Mediated by (5,10,15,20-Tetra-p-tolylporphyrinato)osmium(II) Complexes Organometallics. ,vol. 20, pp. 5189- 5199 ,(2001) , 10.1021/OM010787H
Kathlynn C. Brown, Thomas Kodadek, A transition-state model for the rhodium porphyrin-catalyzed cyclopropanation of alkenes by diazo esters Journal of the American Chemical Society. ,vol. 114, pp. 8336- 8338 ,(1992) , 10.1021/JA00047A081
Michael P. Doyle, Catalytic methods for metal carbene transformations Chemical Reviews. ,vol. 86, pp. 919- 939 ,(1986) , 10.1021/CR00075A013
H.J. Callot, F. Metz, C. Piechocki, Sterically crowded cyclopropanation catalysts. Syn-selectivity using rhodium(III)porphyrins Tetrahedron. ,vol. 38, pp. 2365- 2369 ,(1982) , 10.1016/0040-4020(82)87014-2
H.J. Callot, C. Piechocki, Cyclopropanation using rhodium (III) porphyrins : Large cis vs trans selectivity Tetrahedron Letters. ,vol. 21, pp. 3489- 3492 ,(1980) , 10.1016/S0040-4039(00)78722-3
Jana. Maxwell, Thomas. Kodadek, Organometallic chemistry of porphyrins : spectroscopic and chemical characterization of a rhodium porphyrin-ethyl diazoacetate adduct Organometallics. ,vol. 10, pp. 4- 6 ,(1991) , 10.1021/OM00047A003
Sean O'Malley, Thomas Kodadek, Asymmetric Cyclopropanation of alkenes catalyzed by a “chiral wall” prophyrin Tetrahedron Letters. ,vol. 32, pp. 2445- 2448 ,(1991) , 10.1016/S0040-4039(00)74349-8