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Hoffman, H.M.R.2
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For a recent review on the utility of this class of oxabicycles in synthesis, see: Hartung, I. V.; Hoffmann, H. M. R. Angew. Chem., Int. Ed. 2004, 43. 1934-1949.
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4644345827
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note
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When o-bromostyrene is used, only polymerization of 2a is observed.
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-
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22
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4644363947
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note
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Oligomerization of substrate occurs in these reactions; optimal yields are obtained by slow addition of 2a to a mixture of 1a and the aliphatic olefin.
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23
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0033518572
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(a) Kingsbury, J. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
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(b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
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1642462100
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(c) Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biol. Chem. 2004, 2, 8-23.
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Harrity, J.P.A.7
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26
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3042542346
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and references therein
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Secondary alkyl halides can be readily functionalized by metal-catalyzed cross-coupling reactions. See: Powell, D. A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 7788-7789 and references therein.
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Fu, G.C.2
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4644283514
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note
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Effective dissolution of substrates was achieved with 5 equiv of 3a. Control experiments indicate that high conversion is not due to increased amounts of 3a (5 vs 2 equiv).
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For representative examples, see: (a) Danishefsky, S. J.; Selnick, H. G.; Zelle, R. E.; DeNinno, M. P. J. Am. Chem. Soc. 1988, 110, 4368-4378.
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