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(a) Watson, I. D. G.; Styler, S. A.; Yudin, A. K. J. Am. Chem. Soc. 2004, 126, 5086.
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28
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84957122768
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The Z-configuration was confirmed from a medium coupling constant (7.8 Hz) between the olefinic protons. The E-isomer has 13.2 Hz coupling constant. See also: Mueller, K.; Previdoli, F. Helv. Chim. Acta 1981, 64, 2508.
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Helv. Chim. Acta
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Mueller, K.1
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29
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33748508917
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note
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Pd(II) was found to promote isomerization of 2a into a 55:45 Z/E mixture (THF, room temperature, 72 h).
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30
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0035823881
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3 prevents enamine-to-imine isomerization during enamine formation from primary allylamines: Novak, B. M.; Cafmeyer, J. T. J. Am. Chem. Soc. 2001, 123, 11083.
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Novak, B.M.1
Cafmeyer, J.T.2
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31
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33748486804
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note
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See Supporting Information for details.
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32
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33748507889
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note
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A mechanism involving β-hydride elimination is less likely as it is known to proceed with E-selectivity (see ref 2b).
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33
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33748496114
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note
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A concerted pathway cannot be ruled out at this point.
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