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For an example of an α-redox reaction conducted under biphasic conditions, see
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For a single example of water participating as a nucleophile with the acyl azolium, see: (a) Sohn, S. S.; Bode, J. W. Angew. Chem., Int. Ed. 2006, 45, 6021-6024. For an example of an α-redox reaction conducted under biphasic conditions, see:
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25
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77950413019
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With 5 mol % catalyst, we observe no conversion after 12 h
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With 5 mol % catalyst, we observe no conversion after 12 h.
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27
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(b) Read de Alaniz, J.; Kerr, M. S.; Moore, J. L.; Rovis, T. J. Org. Chem. 2008, 73, 2033-2040.
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77950388578
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Absolute stereochemistry has been assigned by chemical correlation to adducts obtained from phenol addition to the haloaldehydes; see the Supporting Information
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Absolute stereochemistry has been assigned by chemical correlation to adducts obtained from phenol addition to the haloaldehydes; see the Supporting Information.
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30
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77950429945
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A large-scale (1.5 g of cyclopentylmethyldichloroacetaldehyde) reaction affords 2d in 84% yield and 95% ee
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A large-scale (1.5 g of cyclopentylmethyldichloroacetaldehyde) reaction affords 2d in 84% yield and 95% ee.
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36
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(Z)-α-Fluoro-p-methoxyphenylacrylaldehyde provides 4a in 93% ee and 84% yield, while the E substrate provides 4a in 93% ee and 42% yield under identical conditions
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(Z)-α-Fluoro-p-methoxyphenylacrylaldehyde provides 4a in 93% ee and 84% yield, while the E substrate provides 4a in 93% ee and 42% yield under identical conditions.
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Aldehyde purity plays an integral role in the enantioselectivities observed
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Aldehyde purity plays an integral role in the enantioselectivities observed.
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