The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids
作者： Alexander J Blake , Christopher L Friend , Robert J Outram , Nigel S Simpkins , Andrew J Whitehead
DOI: 10.1016/S0040-4039(01)00304-5
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摘要: Abstract The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give α-silylthioester products in good chemical yield and enantiomeric excess values the range 79–93%. absolute configuration one thioester was determined X-ray diffraction.
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sci-hub.se 参考文章(14)
Jens Weiguny, Hans J. Schäfer, Electroorganic synthesis, 57. Synthesis of advanced prostaglandin precursors by Kolbe electrolysis, II. – Preparation of coacids and anodic initiated tandem radical-addition / radical-coupling reaction with (1′R,4′S,3R/S)-3-(cis-4-acetoxycyclopent -2-enyloxy)-3-ethoxypropionic acid Liebigs Annalen der Chemie. ,vol. 1994, pp. 235- 242 ,(1994) , 10.1002/JLAC.199419940303
Michael A. Calter, Catalytic, Asymmetric Dimerization of Methylketene Journal of Organic Chemistry. ,vol. 61, pp. 8006- 8007 ,(1996) , 10.1021/JO961721C
Helmut Buschmann, Hans-Dieter Scharf, Norbert Hoffmann, Peter Esser, The Isoinversion Principle—a General Model of Chemical Selectivity Angewandte Chemie International Edition in English. ,vol. 30, pp. 477- 515 ,(1991) , 10.1002/ANIE.199104771
Ian Fleming, Philip E.J. Sanderson, A one-pot conversion of the phenyldimethylsilyl group into a hydroxyl group Tetrahedron Letters. ,vol. 28, pp. 4229- 4232 ,(1987) , 10.1016/S0040-4039(00)95587-4
William T Brady, Theresa C Cheng, Phenyl(trimethylsilyl)ketene. Some ketene reactions with diazomethane Journal of Organometallic Chemistry. ,vol. 137, pp. 287- 292 ,(1977) , 10.1016/S0022-328X(00)81435-7
Vidya Bhushan, Braj B. Lohray, Dieter Enders, Efficient enantioselective synthesis of allylsilanes by wittig olefination of α-silylaldehydes Tetrahedron Letters. ,vol. 34, pp. 5067- 5070 ,(1993) , 10.1016/S0040-4039(00)60677-9
Charles Fehr, Isabelle Stempf, Jos� Galindo, Enantioselective Addition of Aromatic Thiols to a Ketene Angewandte Chemie. ,vol. 32, pp. 1044- 1046 ,(1993) , 10.1002/ANIE.199310441
H. D. Flack, On enantiomorph‐polarity estimation Acta Crystallographica Section A. ,vol. 39, pp. 876- 881 ,(1983) , 10.1107/S0108767383001762
Horst Pracejus, Organische Katalysatoren, LXI. Asymmetrische Synthesen mit Ketenen, I. Alkaloid-katalysierte asymmetrische Synthesen von α-Phenyl-propionsäureestern Justus Liebigs Annalen der Chemie. ,vol. 634, pp. 9- 22 ,(1960) , 10.1002/JLAC.19606340103
R. J. Anderson, C. A. Henrick, L. D. Rosenblum, General ketone synthesis. Reaction of organocopper reagents with S-alkyl and S-aryl thioesters Journal of the American Chemical Society. ,vol. 96, pp. 3654- 3655 ,(1974) , 10.1021/JA00818A053