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(a) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298-10299.
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3042770459
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Substrate control in the diastereoselective protonation of similar intermediates has been demonstrated: Chow, K. Y.-K.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 8126-8127.
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Patai, S., Rappoport, Z., Eds.; Wiley: New York
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de Kimpe, N.; Verhé, R. The Chemistry of alpha-Haloketones, alpha-Haloaldehdyes and alpha-Haloimines; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1988.
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27
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28444480603
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note
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2,2-Dichloro-(S)-citronellal provides the product in 19% yield and 9:1 dr.
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28
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1842555125
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Letcka et al. have developed a synthesis of α-haloesters based on ketene intermediates: (a) France, S.; Wack, H.; Taggi, A. E.; Hafez, A. M.; Wagerle, T. R.; Shah, M. H.; Dusich, C. L.; Lectka, T. J. Am. Chem. Soc. 2004, 126, 4245-4255.
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France, S.1
Wack, H.2
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Hafez, A.M.4
Wagerle, T.R.5
Shah, M.H.6
Dusich, C.L.7
Lectka, T.8
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29
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0000712093
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(b) Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J.; Lectka, T. Org. Lett. 2001, 3, 2049-2051.
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Hafez, A.M.1
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Wack, H.3
Esterbrook, J.4
Lectka, T.5
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30
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28444438448
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note
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Achiral catalyst: (Diagram presented).
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31
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0004391592
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A values: Br = 0.7; Me = 1.6-1.8. van der Waals radii: Br = 1.95; Me = 2.0. C-X bond lengths: Br = 1.94; Me = 1.54. See: Eliel, E. R.; Haber, R. G. J. Am. Chem. Soc. 1959, 81, 1249-1254.
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Eliel, E.R.1
Haber, R.G.2
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32
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0037462584
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a values: 2-methylphenol = 10.32; 2,6-dibromophenol = 6.6. See: Hanai, T. J. Chromatogr. A 2003, 985, 343-349.
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J. Chromatogr. A
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Hanai, T.1
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33
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1842863015
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Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790-4791.
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Halland, N.1
Braunton, A.2
Bachmann, S.3
Marigo, M.4
Jørgensen, K.A.5
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34
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28444471145
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note
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Under the reported conditions, using 5 mol % of A (1.42 g) and 1a (60 mmol) provided 8.67 g of 2a (55% yield) with 90% ee (62% recovery of excess PhOH).
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