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Trost, B. M.; Fleming, I., Eds.; Pergamon: New York
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Reviews of allyl organometallic addition to C=N bonds: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895. (d) Denmark, S. E.; Nicaise, O. J.-C. J. Chem. Soc., Chem. Commun. 1996, 999. (e) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (f) Kleinman, E. F.; Volkmann, R. A. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I., Eds.; Pergamon: New York, 1991, 975.
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20
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4544259645
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note
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In combination with t-BuOH as proton source, the yield with t-BuBOX improved to 51%, but the enantioselectivity decreased to only 1.8% ee.
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21
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4544305978
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note
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6).
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22
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4544234031
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note
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5b).
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23
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2542556554
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The availability of the Cu-free achiral pathway may contribute to the low enantioselectivity found in reactions employing chiral ligands. For related observations in Cu(II)-catalyzed Mannich-type additions to iminophosphonates, see: Kobayashi, S.; Kiyohara, H.; Nakamura, Y.; Matsubara, R. J. Am. Chem. Soc. 2004, 126, 6558.
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0141789851
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Mechanisms of metal-free reactions involving fluoride activation are distinctly different from those in the presence of Cd(II) or Ag(I), where evidence for regeneration of a metal fluoride by Si-F cleavage has been presented: Aoyama, N.; Hamada, T.; Manabe, K.; Kobayashi, S. J. Org. Chem. 2003, 68, 7329.
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Reviews of nucleophilic activation of allylsilanes: (a) Chuit, C. C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (b) Kennedy, J. W. J.; Hall, D. G. Angew. Chem. Int. Ed. 2003, 42, 4732.
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Chuit, C.C.1
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Reviews of nucleophilic activation of allylsilanes: (a) Chuit, C. C.; Corriu, R. J. P.; Reye, C.; Young, J. C. Chem. Rev. 1993, 93, 1371. (b) Kennedy, J. W. J.; Hall, D. G. Angew. Chem. Int. Ed. 2003, 42, 4732.
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Kennedy, J.W.J.1
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4544301252
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note
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10b).
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Palla, G.; Predieri, G.; Domino, P. Tetrahedron 1986, 42, 3649.
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