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For Cu(II) catalyzed aminohydroxylation of styrenes with oxaziridines to provide 1,3-oxazolidines, with up to 2.5:1 dr and 89% ee, see: Michaelis, D. J.; Ischay, M. A.; Yoon, T. P. J. Am. Chem. Soc. 2008, 130, 6610.
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Phosphine Ligands (e.g., BINAP, dipamp) Inhibit the Reaction
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Phosphine ligands (e.g., BINAP, dipamp) inhibit the reaction.
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Monodentate phosphines provided only crotonaldehyde, resulting from β-hydride elimination. Bidentate ligands with bite angles similar to dppe formed most efficient Ni catalysts for oxazolidine formation
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Monodentate phosphines provided only crotonaldehyde, resulting from β-hydride elimination. Bidentate ligands with bite angles similar to dppe formed most efficient Ni catalysts for oxazolidine formation.
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1H NMR. In the absence of Lewis acid, no reaction is observed
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1H NMR. In the absence of Lewis acid, no reaction is observed.
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34
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80054740814
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Under the optimized conditions with Ni catalyst a series of aryl imine electrophiles reacted in up to 65% ee See Supporting Information
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Under the optimized conditions with Ni catalyst a series of aryl imine electrophiles reacted in up to 65% ee See Supporting Information.
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35
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77956225392
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Palladium-catalyzed synthesis of trans-1,3-oxazolidines in up to 2.3:1 ratio as a racemic mixture
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Palladium-catalyzed synthesis of trans-1,3-oxazolidines in up to 2.3:1 ratio as a racemic mixture: Chen, D.; Chen, X.; Du, T.; Kong, L.; Zhen, R.; Zhen, S.; Wen, Y.; Zhu, G. Tetrahedron Lett. 2010, 51, 5131.
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80054716695
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Isoprene monoxide provided 98% yield and 62% ee. See Supporting Information for details
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Isoprene monoxide provided 98% yield and 62% ee. See Supporting Information for details.
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Several scenarios that involve a kinetic resolution of the vinyl epoxide are possible. For a detailed discussion of such kinetic resolution reactions
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