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Sato, T.1
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(b) For a reagent-controlled, diastereoselective stannyl transfer, see: Enders, D.; Heider, K. J.; Raabe, G. Angew. Chem. Int. Ed. 1993, 32, 598;
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Fleming, I.1
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2: Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065.
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2: Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065.
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2: Lipshutz, B. H.; Reuter, D. C.; Ellsworth, E. L. J. Org. Chem. 1989, 54, 4975.
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2: Lipshutz, B. H.; Reuter, D. C.; Ellsworth, E. L. J. Org. Chem. 1989, 54, 4975.
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2: Oehlschlager, A. C.; Hutzinger, M. W.; Aksela, R.; Sharma, S.; Singh, S. M. Tetrahedron Lett. 1990, 31, 165.
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0032866038
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3MnLi: Usugi, S.; Tang, J.; Shinokubo, H.; Oshima, K. Synlett 1999, 1417.
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3MnLi: Usugi, S.; Tang, J.; Shinokubo, H.; Oshima, K. Synlett 1999, 1417.
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84872952008
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Ley, S. V, Fleming, I, Eds, Thieme: Stuttgart
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Hemeon, I.; Singer, R. D. In Science of Synthesis, Vol. 4; Ley, S. V.; Fleming, I., Eds.; Thieme: Stuttgart, 2002, 205.
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Hemeon, I.1
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3SCN: Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666.
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3SCN: Chenard, B. L.; Laganis, E. D.; Davidson, F.; RajanBabu, T. V. J. Org. Chem. 1985, 50, 3666.
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18
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0343568202
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4NX (X = F, Cl, or Br): Mori, M.; Kaneta, N.; Isono, N.; Shibasaki, M. J. Organomet. Chem. 1993, 455, 255.
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4NX (X = F, Cl, or Br): Mori, M.; Kaneta, N.; Isono, N.; Shibasaki, M. J. Organomet. Chem. 1993, 455, 255.
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19
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48249106554
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2: Honda, T.; Mori, M. Chem. Lett. 1994, 23, 1013.
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2: Honda, T.; Mori, M. Chem. Lett. 1994, 23, 1013.
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25444463326
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[HMIM]Cl (1-hexyl-3-methylimidazolium chloride): Dickson, S.; Dean, D.; Singer, R. D. Chem. Commun. 2005, 4474.
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(c) [HMIM]Cl (1-hexyl-3-methylimidazolium chloride): Dickson, S.; Dean, D.; Singer, R. D. Chem. Commun. 2005, 4474.
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21
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0001392601
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3SnH, see: (a) Nishida, M.; Nishida, A.; Kawahara, N.J. Org. Chem. 1996, 61, 3574.
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3SnH, see: (a) Nishida, M.; Nishida, A.; Kawahara, N.J. Org. Chem. 1996, 61, 3574.
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22
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0001562998
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(b) Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1991, 64, 2585.
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Nozaki, K.1
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Utimoto, K.3
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23
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33748546674
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For conjugate silyl transfer using silyl boronic esters, see: a
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For conjugate silyl transfer using silyl boronic esters, see: (a) Walter, C.; Auer, G.; Oestreich, M. Angew. Chem. Int. Ed. 2006, 45, 5675;
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48249104235
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Angew. Chem. 2006, 118, 5803.
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Angew. Chem
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53249107111
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Angew. Chem. 2008, 120, 3878.
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Angew. Chem
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34547612528
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For conjugate phosphination using silyl phosphines, see
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Chem. Commun
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Trepohl, V.T.1
Oestreich, M.2
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28
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48249148650
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General Procedure for Conjugate Stannylation: Under an inert atmosphere, a flame-dried Schlenk tube was charged with the indicated α,β-unsaturated acceptor A (0.10 mmol, 1.0 equiv) and the THF-H 2O solvent mixture (20:1, 2.1 mL, The base MX (0.1 mmol, 1.0 equiv) as well as B (1, 0.25 mmol, 2.5 equiv) were added, and the reaction mixture was heated to 50 °C. Conversion was monitored by TLC. After full consumption of A the reaction mixture was diluted with tert-butylmethylether (10 mL) at r.t. A small portion of silica gel was added and the solvents were removed in vacuo. The crude product C on silica gel was then subjected to flash chromatography on Et3N-deactivated silica gel using cyclohexane-tert-butylmethylether solvent mixtures. Stannanes C 22-95, were isolated as colorless oils
-
3N-deactivated silica gel using cyclohexane-tert-butylmethylether solvent mixtures. Stannanes C (22-95%) were isolated as colorless oils.
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29
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48249087212
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Reagent 1 is not particularly volatile, stable towards GLC measurements, and provides easy-to-interpret NMR spectra.
-
Reagent 1 is not particularly volatile, stable towards GLC measurements, and provides easy-to-interpret NMR spectra.
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30
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48249158184
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Preparation of Dimethylphenyl(trimethylsilyl)stannane (1, Neat dimethylphenylstannyl chloride19 (3.00 g, 11.5 mmol, 1.00 equiv) was added dropwise to Me3SiCl-activated lithium (large excess) in THF (40 mL) at 0 °C under ultrasonic irradiation, and the reaction mixture was then maintained at these conditions for 2 h. The supernatant blue-black-colored solution was subsequently transferred to another flask and slowly treated with trimethylsilyl chloride (3.10 mL, 24.3 mmol, 2.10 equiv) at 0 °C. After stirring at ambient temperature for additional 3 h, the solvent was removed under reduced pressure. Crude 1 was purified by flash chromatography on silica gel using cyclohexane as solvent. The title compound (3.22 g, 10.8 mmol, 94, was obtained as a colorless oil. IR (ATR, 3062 (w, 2950 (w, 2893 (w, 1427 (m) cm-1. 1H NMR 300 MHz, CDCl3, δ, 0.26 [t, 2JH,Sn, 2
-
20SiSn: C, 44.18; H, 6.74. Found: C, 44.30; H, 7.01.
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31
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0343500782
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Sakai, T.; Miyata, K.; Utaka, M.; Takeda, A. Bull. Chem. Soc. Jpn. 1987, 60, 1063.
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48249152108
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0001425862
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Kitching, W.; Olszowy, H. A.; Harvey, K. J. Org. Chem. 1982, 47, 1893.
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Kitching, W.1
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