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See for example: Sibi, M. P.; Liu, P.; Ji, J.; Hajra, S.; Chen, J.-X. J. Org. Chem. 2002, 67, 1738.
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Chen, J.-X.5
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0003536850
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Pergamon Press: Oxford
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Esters are known to prefer the s-trans conformation which does not possess the correct geometry for cyclization. See: (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1984.
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Deslongchamps, P.1
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5
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0034669646
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(c) For a radical cyclization concerning an ester precursor, see for example: Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omoto, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041.
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Yorimitsu, H.1
Nakamura, T.2
Shinokubo, H.3
Oshima, K.4
Omoto, K.5
Fujimoto, H.6
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6
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0037819327
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Norrby, P.-O.; Mader, M. M.; Vitale, M.; Prestat, G.; Poli, G. Organometallics 2003, 22, 1849.
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Organometallics
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Norrby, P.-O.1
Mader, M.M.2
Vitale, M.3
Prestat, G.4
Poli, G.5
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7
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31944443083
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3-allyl complex. In this case, the Pd-catalyzed cleavage of the malonyl moiety from the substrate might take place either before or after the C-C bond formation. See also: Silvestri, M. A.; He, C.; Khoram, A.; Lepore, S. D. Tetrahedron Lett. 2006, 47, 1625.
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Silvestri, M.A.1
He, C.2
Khoram, A.3
Lepore, S.D.4
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(b) Commandeur, C.; Thorimbert, S.; Malacria, M. J. Org. Chem. 2003, 68, 5588.
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Commandeur, C.1
Thorimbert, S.2
Malacria, M.3
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10
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0344875121
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(c) Branchadell, V.; Moreno-Mañas, M.; Pleixats, R.; Thorimbert, S.; Commandeur, C.; Boglio, C.; Malacria, M. J. Organomet. Chem. 2003, 687, 337.
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Branchadell, V.1
Moreno-Mañas, M.2
Pleixats, R.3
Thorimbert, S.4
Commandeur, C.5
Boglio, C.6
Malacria, M.7
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11
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8644236493
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(d) Thorimbert, S.; Tailler, C.; Bareyt, S.; Humilière, D.; Malacria, M. Tetrahedron Lett. 2004, 45, 9123.
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Thorimbert, S.1
Tailler, C.2
Bareyt, S.3
Humilière, D.4
Malacria, M.5
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12
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27644439966
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(e) Boglio, C.; Stahike, S.; Thorimbert, S.; Malacria, M. Org. Lett. 2005, 7, 4851.
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Boglio, C.1
Stahike, S.2
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Malacria, M.4
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13
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33748688335
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note
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3Si group to be almost orthogonal to the C=C, whereas the distal allylic C-O bond is not expected to suffer such a restriction. Since the oxidative addition of Pd(0) to allylic acetates is known to be operative only if the substrate can adopt an orthogonal C=C/C-O disposition (ref. 7b) it appears that the silylated substrates 6 might be intrinsically biased to expel the vicinal rather than the distal allylic leaving group.
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15
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33748705475
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note
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Substrates 6a-c were easily prepared in a few steps starting from butyn-1,4-diol.
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16
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33748698348
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note
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1H NMR of the crude products as well as TLC analysis indicate complete disappearance of the starting material and the absence of other possible regio- or stereoisomers of 7. Partial decomposition of the starting material as polymeric material is thus likely.
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17
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33748703208
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note
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4Si: 285.1522; found: 285.1523.
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21
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0038675907
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Negishi, E., Ed.; Wiley-Interscience: New York
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(d) Hiyama, T.; Shirakawa, E. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002, 285-301.
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Handbook of Organopalladium Chemistry for Organic Synthesis
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Hiyama, T.1
Shirakawa, E.2
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23
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33748695709
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Dietrich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Chap. 4
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(b) Mitchell, T. N. In Metal-Catalysed Cross-Coupling Reactions; Dietrich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 4.
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Metal-Catalysed Cross-Coupling Reactions
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Mitchell, T.N.1
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26
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33748677826
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Dietrich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Chap. 2
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(c) Suzuki, A. In Metal-Catalysed Cross-Coupling Reactions; Dietrich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, Chap. 2.
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(1998)
Metal-Catalysed Cross-Coupling Reactions
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Suzuki, A.1
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0036003102
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Hosoi, K.; Nozaki, K.; Hiyama, T. Chem. Lett. 2002, 2, 138.
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Hosoi, K.1
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Hiyama, T.3
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28
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33748702200
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note
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2 and the resulting organic layer was washed with brine and dried. Removal of the solvent under reduced pressure gave the crude products 10a-g, which were purified via flash chromatography.
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29
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33748714443
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note
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Hiyama couplings involving 1,2-disubstituted vinylsilanes do not show the same trend. See for example ref. 12.
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31
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0344443286
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(b) Lemaire, S.; Prestat, G.; Giambastiani, G.; Madec, D.; Pacini, B.; Poli, G. J. Organomet. Chem. 2003, 687, 291.
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Lemaire, S.1
Prestat, G.2
Giambastiani, G.3
Madec, D.4
Pacini, B.5
Poli, G.6
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