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Recently, a chelation-assisted intramolecular hydroacylation using a (butenylsulfanyl)benzaldehyde yielding medium-sized heterocycles has been developed, see: H. D. Bendorf, C. M. Colella, E. C. Dixon, M. Marchetti, A. N. Matukonis, J. D. Musselman, T. A. Tiley, Tetrahedron Lett. 2002, 43, 7031-7034.
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Recently, a chelation-assisted intramolecular hydroacylation using a (butenylsulfanyl)benzaldehyde yielding medium-sized heterocycles has been developed, see: H. D. Bendorf, C. M. Colella, E. C. Dixon, M. Marchetti, A. N. Matukonis, J. D. Musselman, T. A. Tiley, Tetrahedron Lett. 2002, 43, 7031-7034.
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43
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23244446232
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[13b]
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[13b]
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44
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34547184735
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Dppf has been successfully used as ligand in the hydroacylation of salicylaldehyde and triethylvinylsilane, see ref.[13b
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[13b]
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45
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34547189915
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4 forms a cationic Rh-complex due to the precipitation of AgCl.
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4 forms a cationic Rh-complex due to the precipitation of AgCl.
-
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46
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34547144995
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S-Phos=2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl.
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S-Phos=2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl.
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47
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34547173888
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This type of base-induced isomerization was also observed by Suemune and Tanaka, see ref.[17
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[17]
-
-
-
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49
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34547161660
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These ligands (except phosphoramidite 19, see Experimental Section) are either commercially available (8, 16, 17, 25 and 27) and/or were prepared following literature procedures; for 9, 16, 17 and 18: a) A. H. M. de Vries, A. Meetsma, B. L. Feringa, Angew. Chem. 1996, 108, 2526-2528;
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52
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13244251142
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for compounds 21 and 22: c H. Bernsmann, M. van den Berg, R. Hoen, A. J. Minnaard, G. Mehler, M. T. Reetz, J. G. De Vries, B. L. Feringa, J. Org. Chem. 2005, 70, 943-951;
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53
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34547148167
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for ligand 20: d W. Zhang, X. Zhang, Angew. Chem. 2006, 118, 5641-5644;
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for ligand 20: d) W. Zhang, X. Zhang, Angew. Chem. 2006, 118, 5641-5644;
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8744260916
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for ligands 23 and 24: e Y. Xu, N. W. Alcock, G. J. Clarkson, G. Docherty, G. Woodward, M. Wills, Org. Lett. 2004, 6, 4105-4107;
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61
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for compound 25: i A. Alexakis, J. Burton, J. Vastra, C. Benhaim, X. Fournioux, A. van den Heuvel, J.-M. Levêque, F. Maze, S. Rosset, Eur. J. Org. Chem. 2000, 4011-4027;
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34547205316
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64
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34547164159
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This observation was also made by Suemune and Tanaka, see ref, 15
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34547152427
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An alternative explanation could be that in the case of bidentate (and sterically demanding) ligands the coordination of norbornadiene to rhodium might be inhibited completely and therefore the attack of the free norbornadiene would proceed in an exo-like fashion
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An alternative explanation could be that in the case of bidentate (and sterically demanding) ligands the coordination of norbornadiene to rhodium might be inhibited completely and therefore the attack of the free norbornadiene would proceed in an exo-like fashion.
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