Computational Studies on Osmium-Catalyzed Olefin Oxidation Reactions

作者: Dominik Munz , Alexander Poethig , Thomas Strassner

DOI: 10.1007/978-3-642-25258-7_6

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摘要: The oxidative functionalization of olefins is an important reaction for organic synthesis as well the industrial production bulk chemicals. Various processes have been explored, among them also metal-catalyzed methods using strong oxidants like osmium tetroxide. Especially, asymmetric dihydroxylation by osmium(VIII) complexes has proven to be a valuable synthetic chemist. A large number experimental studies had conducted, but mechanisms various osmium-catalyzed reactions remained controversial issue. This changed when density functional theory calculations became available and computational helped unravel open mechanistic questions. mini review will focus on recent osmium-mediated oxidation alkenes.

参考文章(109)
H.Z. Sable, K.A. Powell, H. Katchian, C.B. Niewoehner, S.B. Kadlec, Studies on cyclitols—XV Tetrahedron. ,vol. 26, pp. 1509- 1524 ,(1970) , 10.1016/S0040-4020(01)92980-1
P. Jeffrey Hay, Willard R. Wadt, Ab initio effective core potentials for molecular calculations. Potentials for K to Au including the outermost core orbitals Journal of Chemical Physics. ,vol. 82, pp. 299- 310 ,(1985) , 10.1063/1.448975
Koichiro Oshima, K. Barry Sharpless, Anthony O. Chong, Synthesis of dioxobis(tert-alkylimido)osmium(VIII) and oxotris(tert-alkylimido)osmium(VIII) complexes. Stereospecific vicinal diamination of olefins Journal of the American Chemical Society. ,vol. 99, pp. 3420- 3426 ,(1977) , 10.1021/JA00452A039
Alexander Poethig, Thomas Strassner, The Mechanism of the Permanganate-Promoted Oxidative Cyclization of 1,5-Dienes - a DFT Study Collection of Czechoslovak Chemical Communications. ,vol. 72, pp. 715- 727 ,(2007) , 10.1135/CCCC20070715
Timothy J Donohoe, Jonathan J.G Winter, Madeleine Helliwell, Geoffrey Stemp, Hydrogen bonding control in the oxidative cyclisation of 1,5-dienes Tetrahedron Letters. ,vol. 42, pp. 971- 974 ,(2001) , 10.1016/S0040-4039(00)02225-5
Ulrich Koert, Stereoselective Synthesis of Oligo-Tetrahydrofurans Synthesis. ,vol. 1995, pp. 115- 132 ,(1995) , 10.1055/S-1995-3883
Hilde Rubinstein, John S. Svendsen, Ingjerd Hollingsæter, Man Shun Soon Huang, Thorleif Anthonsen, Hari N. Pati, Kirpal S. Bisht, Virinder S. Parmar, George W. Francis, ENANTIOSELECTIVE AMINOHYDROXYLATION OF ALKENES Acta Chemica Scandinavica. ,vol. 48, pp. 439- 444 ,(1994) , 10.3891/ACTA.CHEM.SCAND.48-0439
Christian Döbler, Gerald M. Mehltretter, Uta Sundermeier, Matthias Beller, Dihydroxylation of olefins using air as the terminal oxidant Journal of Organometallic Chemistry. ,vol. 621, pp. 70- 76 ,(2001) , 10.1016/S0022-328X(00)00856-1
Donald W. Patrick, Larry K. Truesdale, Scott A. Biller, K. Barry Sharpless, Stereospecific vicinal oxyamination of olefins by alkylimidoosmium compounds Journal of Organic Chemistry. ,vol. 43, pp. 2628- 2638 ,(1978) , 10.1021/JO00407A016