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Otera, J., Ed.; Wiley-VHC: Weinheim, Chapter 10
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For recent reviews on allylation of aldehydes and imines, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
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Denmark, S.E.1
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0036666324
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Otera, J., Ed.; Wiley-VHC: Weinheim, Chapter 11
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For recent reviews on allylation of aldehydes and imines, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
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Modern Carbonyl Chemistry
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Chemler, S.R.1
Roush, R.W.2
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4
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0000862669
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For recent reviews on allylation of aldehydes and imines, see: (a) Puentes, C. O.; Kouznetsov, V. J. Heterocycl. Chem. 2002, 39, 595. (b) Denmark, S. E.; Almstead, N. G. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 10. (c) Chemler, S. R.; Roush, R. W. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VHC: Weinheim, 2000; Chapter 11. (d) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
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9
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14844358754
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note
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Without removing water, reactions become dirty (many tailing spots on TLC) and no allylation products are detected.
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11
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0001374863
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2Zn (240 mol %) in THF (3 mL) - n-hexane (1.2 mL) at room temperature, α- and γ-methylallyl alcohols (1 mmol) react with benzaldehyde (1.2 mmol) to provide mixtures of anti- and syn-2-methyl-1-phenyl- 3-buten-1-ols in the same ratio (2.4:1). The same reactions with α- and γ-phenylallyl alcohols provide anti- and syn-1,2-diphenyl-3-buten-1-ols in the same, but in higher ratios of 10:1: Tamaru, Y. J. Organomet. Chem. 1999, 576, 215.
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14844359457
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note
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Under present conditions, 1,3-disubstituted allylic alcohols, such as 1,3-dimethylallyl alcohols and 2-cyclohexenol, failed to give expected homoallylamines.
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14
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14844346822
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note
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Crystallographic data (excluding structure factors) for the structure of 2 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-256123. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road. Cambridge CB21EZ. UK (fax: (+44)1223-336-033; e-mail: deposit@ ccdc.cam.ac.uk).
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14844363474
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note
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Allylation with allyl alcohol was reported for benzaldehyde-imine using an umpolung technique of π-allylpalladium with indium(I) iodide. Allyl bromide, iodide, acetate, and carbonate showed good yields; however chloride and alcohol moderate and poor yields, respectively. See ref 12b.
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26
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