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1
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0030007621
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For comprehensive reviews on the Tamao-Fleming oxidation see: (a) Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
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Jones, G.R.1
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7
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5644227519
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Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart
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(c) Singer, R. D. In Science of Synthesis, Vol. 4; Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart, 2002, 231.
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Singer, R.D.1
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(b) Ager, D. J.; Fleming, I.; Patel, S. K. J. Chem. Soc., Perkin Trans. 1 1981, 2520.
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Ager, D.J.1
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Patel, S.K.3
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(c) Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans. 1 1981, 2527.
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Fleming, I.1
Newton, T.W.2
Roessler, F.3
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2SiCu(CN)Li see: Tamao, K.; Kawachi, A.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 3989.
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Tamao, K.1
Kawachi, A.2
Ito, Y.3
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18
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(a) Tückmantel, W.; Oshima, K.; Nozaki, H. Chem. Ber. 1986, 119, 1581.
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Tückmantel, W.1
Oshima, K.2
Nozaki, H.3
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19
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37049081703
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(b) Crump, R. A. N. C.; Fleming, I.; Urch, C. J. J. Chem. Soc., Perkin Trans 1 1994, 701.
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Crump, R.A.N.C.1
Fleming, I.2
Urch, C.J.3
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21
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0032577035
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Lipshutz, B. H.; Sclafani, J. A.; Takanami, T. J. Am. Chem. Soc. 1998, 720, 4021.
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Lipshutz, B.H.1
Sclafani, J.A.2
Takanami, T.3
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(a) Ito, H.; Ishizuka, T.; Tateiwa, J.-i.; Sonoda, M.; Hosomi, A. J. Am. Chem. Soc. 1998, 720, 11196.
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Ito, H.1
Ishizuka, T.2
Tateiwa, J.-I.3
Sonoda, M.4
Hosomi, A.5
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23
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5644295537
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(b) See also: Clark, C. T.; Lake, J. F.; Scheldt, K. A. J. Am. Chem. Soc. 2004, 726, 85.
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Clark, C.T.1
Lake, J.F.2
Scheldt, K.A.3
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24
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33845280789
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(c) For other catalyst systems see: Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc. 1988, 770, 5579.
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Hayashi, T.1
Matsumoto, Y.2
Ito, Y.3
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25
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0037009992
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(d) Ogoshi, S.; Tomiyasu, S.; Morita, M.; Kurosawa, H. J. Am. Chem. Soc. 2002, 124, 11598.
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Ogoshi, S.1
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Morita, M.3
Kurosawa, H.4
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26
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34248152109
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Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart
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Hameon, I.; Singer, R. D. In Science of Synthesis, Vol. 4; Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart, 2002, 225.
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Hameon, I.1
Singer, R.D.2
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27
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0008757976
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For a single report on the preparation of 3 and an application in a silyl metalation reaction see: Morizawa, Y.; Oda, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 1163; this seminal publication also includes the magnesium reagent 7.
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Tetrahedron Lett.
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Morizawa, Y.1
Oda, H.2
Oshima, K.3
Nozaki, H.4
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28
-
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5644233879
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note
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2O) was added accompanied by a color change from red to yellowish brown. The reaction mixture was maintained at this temperature for further 15 min and was ready to use.
-
-
-
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29
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5644227520
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note
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4), the solvents were evaporated under reduced pressure and the resulting crude product 5 was purified by flash chromatography on silica gel using cyclohexane-MTBE solvent mixtures,
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-
-
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30
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5644302350
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note
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4Cl (25 mL). Work-up and purification of 5 as described for Method A.
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-
-
-
31
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5644249421
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-
note
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2.
-
-
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-
32
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5644267904
-
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note
-
3SiZnCl under copper catalysis.
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-
-
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33
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33746803229
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3SiLi undergoes rapid 1,4-additon to β-monosubstituted ketones in the absence of any copper catalyst. See: Still, W. C. J. Org. Chem. 1976, 41, 3063.
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(1976)
J. Org. Chem.
, vol.41
, pp. 3063
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Still, W.C.1
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34
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5644272804
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note
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2SiLi (2).
-
-
-
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35
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0141581512
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Krause, N., Ed.; Wiley-VCH: Weinheim
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2 is believed to be reduced in situ as described for the conjugate addition of dialkylzincs: Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modem Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002, 224.
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Modem Organocopper Chemistry
, pp. 224
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Feringa, B.L.1
Naasz, R.2
Imbos, R.3
Arnold, L.A.4
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38
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0024826452
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(c) Horiguchi, Y.; Komatsu, M.; Kuwajima, I. Tetrahedron Lett. 1989, 30, 7087.
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(1989)
Tetrahedron Lett.
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, pp. 7087
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Horiguchi, Y.1
Komatsu, M.2
Kuwajima, I.3
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39
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0025012515
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(d) Alexakis, A.; Sedrani, R.; Mangeney, P. Tetrahedron Lett. 1990, 31, 345.
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(1990)
Tetrahedron Lett.
, vol.31
, pp. 345
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Alexakis, A.1
Sedrani, R.2
Mangeney, P.3
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40
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5644271618
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note
-
The generation of 3 from 1 produces a fourfold excess of LiCl, which might function as a Lewis acid.
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