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35048888173
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6 (3-5 mol %, M = 343.6) in distilled THF or dioxane (2.5 M) was stirred under an argon atmosphere at room temperature for 3 min. The aminonucleophile (3 equiv) and then the enyne (1 equiv) were finally added. After completion of the reaction, the mixture was filtered through a short pad of silica gel (EtOAc) and the solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash chromatography.
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6 (3-5 mol %, M = 343.6) in distilled THF or dioxane (2.5 M) was stirred under an argon atmosphere at room temperature for 3 min. The aminonucleophile (3 equiv) and then the enyne (1 equiv) were finally added. After completion of the reaction, the mixture was filtered through a short pad of silica gel (EtOAc) and the solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash chromatography.
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46
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33244484834
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and references cited therein
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35048878409
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TPPTS: tris(m-sulfonatophenyl)phosphane trisodium salt
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(a) TPPTS: tris(m-sulfonatophenyl)phosphane trisodium salt.
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50
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2342498777
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Paquette, L, Fuchs, P, Crich, D, Wipf, P, Eds, Wiley: New York
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(d) Michelet, V.; Savignac, M.; Genêt, J.-P. Electronic Encyclopedia of Reagents for Organic Synthesis; Paquette, L., Fuchs, P., Crich, D., Wipf, P., Eds.; Wiley: New York, 2004.
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For references dealing with the trapping of cyclopropylcarbenes of type A, see: a
-
For references dealing with the trapping of cyclopropylcarbenes of type A, see: (a) Nieto-Oberhuber, C.; Lopez, S.; Paz Munoz, M.; Jimenez-Nunez, E.; Bunuel, E.; Cardenas, D. J.; Echavarren, A. M. Chem.-Eur. J. 2006, 12, 1694.
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(b) Lopez, S.; Herrero-Gomez, E.; Perez-Galan, P.; Nieto-Oberhuber, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 6029.
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55
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35048871226
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A mechanism relying on a concerted diastereoselective hydroamination/carbocyclization sequence leading directly to vinylaurate intermediate B cannot be ruled out
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A mechanism relying on a concerted diastereoselective hydroamination/carbocyclization sequence leading directly to vinylaurate intermediate B cannot be ruled out.
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