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2, see: c Y. Gao, M. Shirai, F. Sato, Tetrahedron Lett. 1997, 38, 6849-6852.
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2, see: c) Y. Gao, M. Shirai, F. Sato, Tetrahedron Lett. 1997, 38, 6849-6852.
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For a recent review of transition-metal-catalyzed reactions in the synthesis of heterocycles, see
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Control of regioselectivity in bimolecular metal-mediated coupling reactions between internal alkynes and imines has been possible in only a small subset of reactions, whereby the origin of selectivity is derived by steric or electronic effects; for zirconium-mediated coupling, see: a S. L. Buchwald, B. T. Watson, M. W. Wannamaker, J. C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486-4494;
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Control of regioselectivity in bimolecular metal-mediated coupling reactions between internal alkynes and imines has been possible in only a small subset of reactions, whereby the origin of selectivity is derived by steric or electronic effects; for zirconium-mediated coupling, see: a) S. L. Buchwald, B. T. Watson, M. W. Wannamaker, J. C. Dewan, J. Am. Chem. Soc. 1989, 111, 4486-4494;
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b) R. B. Grossman, W. M. Davis, S. L. Buchwald, J. Am. Chem. Soc. 1991, 113, 2321-2322;
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Grossman, R.B.1
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for titanium-mediated coupling, see: c
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for titanium-mediated coupling, see: c) Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913-5916;
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0242432936
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for nickel-mediated coupling, see: e
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for nickel-mediated coupling, see: e) S. J. Patel, T. F. Jamison, Angew. Chem. 2003, 115, 1402-1405;
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Angew. Chem. Int. Ed. 2003, 42, 1364-1367;
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Angew. Chem. Int. Ed. 2004, 43, 3941-3944;
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23844494674
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for rhodium-mediated coupling, see: g
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for rhodium-mediated coupling, see: g) J.-R. Kong, C.-W. Cho, M. J. Krische, J. Am. Chem. Soc. 2005, 127, 11269-11276.
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Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913-5916; see also Ref. [9];
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a) Y. Gao, K. Harada, F. Sato, Tetrahedron Lett. 1995, 36, 5913-5916; see also Ref. [9];
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28
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0037467387
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for an example of a unique nickel-catalyzed reductive coupling with TMS-C=C-Ph and nPrCHO that provides similar regioselectivity, see: b K. M. Miller, W.-S. Huang, T. F. Jamison, J. Am. Chem. Soc. 2003, 125, 3442-3443.
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for an example of a unique nickel-catalyzed reductive coupling with TMS-C=C-Ph and nPrCHO that provides similar regioselectivity, see: b) K. M. Miller, W.-S. Huang, T. F. Jamison, J. Am. Chem. Soc. 2003, 125, 3442-3443.
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34250763688
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An aromatic heterocycle was tolerated on the imine, yet yields in the coupling reaction with 2-furylbenzylimine were uniformly lower 23 , than those between homopropargylic alkoxides and imines 7, 16, 21, 23 and 25; for details, see the Supporting Information
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An aromatic heterocycle was tolerated on the imine, yet yields in the coupling reaction with 2-furylbenzylimine were uniformly lower (23 %) than those between homopropargylic alkoxides and imines 7, 16, 21, 23 and 25; for details, see the Supporting Information.
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2 minimized scrambling of the γ stereocenter.
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2 minimized scrambling of the γ stereocenter.
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32
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84986534354
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For an alternative coupling reaction of imines with fumarates in the synthesis of α,β-unsaturated γ-lactams, see
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For an alternative coupling reaction of imines with fumarates in the synthesis of α,β-unsaturated γ-lactams, see: J. Barluenga, F. Palacios, S. Fustero, V. Gotor, Synthesis 1981, 200-201.
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