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For reviews of allylmetal additions to carbonyl compounds, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
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Trost, B.M., Ed.; Pergamon Press: Oxford
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(b) Roush, W.R. In Comprehensive Organic Synthesis, Trost, B.M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 1.
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Roush, W.R.1
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For reviews of the addition of allylic tin reagents to carbonyl compounds, see: (a) Marshall, J.A. Chem. Rev. 1996, 96, 31.
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Marshall, J.A.1
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(b) Nishigaichi, Y.; Takuwa, A.; Naruja, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395.
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Nishigaichi, Y.1
Takuwa, A.2
Naruja, Y.3
Maruyama, K.4
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5
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3
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3: Aspinall, H.C.; Browning, A.F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639.
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Aspinall, H.C.1
Browning, A.F.2
Greeves, N.3
Ravenscroft, P.4
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2: Cozzi, P.G.; Floriani, C.; Chiesi-Villa, A.; Rizzoli, C. Synlett 1994, 857.
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Cozzi, P.G.1
Floriani, C.2
Chiesi-Villa, A.3
Rizzoli, C.4
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4NCl or HMPA): Yano, K.; Baba, A.; Matsuda, H. Bull. Chem. Soc. Jpn. 1992, 65, 66.
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Yano, K.1
Baba, A.2
Matsuda, H.3
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10
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0027501692
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For a highly effective catalytic enantioselective allylation based on a titanium/BINOL complex, see: (a) Keck, G.E.; Geraci, L.S. Tetrahedron Lett. 1993, 34, 7827.
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Tetrahedron Lett.
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Keck, G.E.1
Geraci, L.S.2
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(b) Costa, A.L.; Piazza, M.G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001.
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Costa, A.L.1
Piazza, M.G.2
Tagliavini, E.3
Trombini, C.4
Umani-Ronchi, A.5
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Aoki, S.; Mikami, K.; Terada, M.; Nakai, T. Tetrahedron 1993, 49, 1783.
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Tetrahedron
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Aoki, S.1
Mikami, K.2
Terada, M.3
Nakai, T.4
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14
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33751155896
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For related discussions, see references 3e, 5, and: (a) Scholl, M.; Lim, C-K; Fu, G.C. J. Org. Chem. 1995, 60, 6229.
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Lim, C.-K.2
Fu, G.C.3
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0343826519
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Paquette, L.A., Ed.; John Wiley and Sons: Chichester
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For a review of the preparation and reactions of allyldibutyltin chloride, see: Tagliavini, G. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L.A., Ed.; John Wiley and Sons: Chichester, 1995; Vol. 1, p 98.
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Encyclopedia of Reagents for Organic Synthesis
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Tagliavini, G.1
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0343826517
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Boaretto, A.; Marton, D.; Tagliavini, G. J. Organomet. Chem. 1985, 288, 283.
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Boaretto, A.1
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18
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35448975836
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For other examples of exchange reactions between tin alkoxides and silicon or acid halides, see note 6 and: (a) Leigh, D.A.; Martin, R.P.; Smart, J.P.; Truscello, A.M. J. Chem. Soc., Chem. Commun. 1994, 1373.
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Truscello, A.M.4
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19
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0037559838
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(b) Reginato, G.; Ricci, A.; Roelens, S.; Scapecci, S. J. Org. Chem. 1990, 55, 5132.
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Reginato, G.1
Ricci, A.2
Roelens, S.3
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20
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85025748053
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Gambaro, A.; Peruzzo, V.; Plazzogna, G.; Tagliavini, G. J. Organomet. Chem. 1980, 197, 45.
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Gambaro, A.1
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Plazzogna, G.3
Tagliavini, G.4
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22
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85030205334
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note
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2) or elution through a short plug of Florisil® with Skelly B (silyl ethers) afforded the pure alcohol derivatives as colorless oils.
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23
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85030206294
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note
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1H NMR spectroscopy of the crude reaction mixture. The exchange reaction in eq 5 may not be favorable under these conditions.
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24
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85030205930
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note
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(formula presented)
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25
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85030210341
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note
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The following electrophiles provided no protected product in the case of benzaldehyde: methyl iodide; methanesulfonyl chloride; and t-butyldimethylsilyl chloride. Chloromethyl methyl ether gave complex mixures in the presence and absence of catalyst. The use of trimethylsilyl chloride with cinnamaldehyde and cyclohexanecarboxaldehyde gave product mixtures.
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26
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85030205621
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note
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4. Evaporation of solvent (residual water was usually present, but no attempt was made to remove it) followed by chromatography of the residue (5:1 Skelly B / EtOAc) yielded the alcohol products as colorless oils.
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