-
9
-
-
0002324898
-
-
Fleming, I.; Dunogues, J.; Smithers, R. Org. React. 1989, 37, 57.
-
(1989)
Org. React
, vol.37
, pp. 57
-
-
Fleming, I.1
Dunogues, J.2
Smithers, R.3
-
10
-
-
0001579610
-
-
Trost, B. M, Fleming, I, Paquette, L. A, Eds, Pergamon: Oxford
-
(j) Fleming, I. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds.; Pergamon: Oxford, 1991, 563.
-
(1991)
Comprehensive Organic Synthesis
, vol.2
, pp. 563
-
-
Fleming, I.1
-
14
-
-
0025029262
-
-
For reviews concerning the synthesis of allylsilanes, see
-
(a) For reviews concerning the synthesis of allylsilanes, see: Sarkar, T. K. Synthesis 1990, 969.
-
(1990)
Synthesis
, pp. 969
-
-
Sarkar, T.K.1
-
16
-
-
0343011976
-
-
To see some examples of the synthesis of E-allylsilanes: Tanigawa, Y.; Fuse, Y.; Murahashi, S.-I. Tetrahedron Lett. 1982, 23, 557.
-
To see some examples of the synthesis of E-allylsilanes: Tanigawa, Y.; Fuse, Y.; Murahashi, S.-I. Tetrahedron Lett. 1982, 23, 557.
-
-
-
-
17
-
-
0027293154
-
-
Bhushan, V.; Lohray, B. B.; Enders, D. Tetrahedron Lett. 1993, 34, 5067.
-
(1993)
Tetrahedron Lett
, vol.34
, pp. 5067
-
-
Bhushan, V.1
Lohray, B.B.2
Enders, D.3
-
19
-
-
0000047923
-
-
(f) Suginome, M.; Matsumoto, A.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3061.
-
(1996)
J. Am. Chem. Soc
, vol.118
, pp. 3061
-
-
Suginome, M.1
Matsumoto, A.2
Ito, Y.3
-
20
-
-
0000013281
-
-
(g) Hanamoto, T.; Sugino, A.; Kikukawa, T.; Inanaga, J. Bull. Soc. Chim. Fr. 1997, 134, 391.
-
(1997)
Bull. Soc. Chim. Fr
, vol.134
, pp. 391
-
-
Hanamoto, T.1
Sugino, A.2
Kikukawa, T.3
Inanaga, J.4
-
21
-
-
2442719958
-
-
(h) Kamachi, T.; Kuno, A.; Matsuno, C.; Okamoto, S. Tetrahedron Lett. 2004, 45, 4677.
-
(2004)
Tetrahedron Lett
, vol.45
, pp. 4677
-
-
Kamachi, T.1
Kuno, A.2
Matsuno, C.3
Okamoto, S.4
-
22
-
-
4644306525
-
-
Hodgson, D. M.; Fleming, M. J.; Stanway, S. J. J. Am. Chem. Soc. 2004, 126, 12250.
-
(2004)
J. Am. Chem. Soc
, vol.126
, pp. 12250
-
-
Hodgson, D.M.1
Fleming, M.J.2
Stanway, S.J.3
-
23
-
-
0343497754
-
-
Ilio, H.; Ishii, M.; Tsukamoto, T. Tetrahedron Lett. 1988, 29, 5965.
-
(1988)
Tetrahedron Lett
, vol.29
, pp. 5965
-
-
Ilio, H.1
Ishii, M.2
Tsukamoto, T.3
-
26
-
-
37049088613
-
-
(b) Fleming, I.; Gil, S.; Sarkar, A. K. J. Chem. Soc., Perkin Trans, 1 1992, 3351.
-
(1992)
J. Chem. Soc., Perkin Trans, 1
, pp. 3351
-
-
Fleming, I.1
Gil, S.2
Sarkar, A.K.3
-
27
-
-
0000537482
-
-
(a) Obora, Y.; Tsuji, Y.; Kobayashi, M.; Kawamura, T. J. Org. Chem. 1995, 60, 4647.
-
(1995)
J. Org. Chem
, vol.60
, pp. 4647
-
-
Obora, Y.1
Tsuji, Y.2
Kobayashi, M.3
Kawamura, T.4
-
28
-
-
0027939290
-
-
(b) Landais, Y.; Planchenault, D.; Weber, V. Tetrahedron Lett. 1994, 35, 9549.
-
(1994)
Tetrahedron Lett
, vol.35
, pp. 9549
-
-
Landais, Y.1
Planchenault, D.2
Weber, V.3
-
29
-
-
0033549735
-
-
Concellón, J. M.; Bernad, P. L.; Pérez-Andrés, J. A. Angew. Chem. Int. Ed. 1999, 38, 2384.
-
(1999)
Angew. Chem. Int. Ed
, vol.38
, pp. 2384
-
-
Concellón, J.M.1
Bernad, P.L.2
Pérez-Andrés, J.A.3
-
30
-
-
0000363311
-
-
Concellón, J. M.; Bernad, P. L.; Bardales, E. Org. Lett. 2001, 3, 937.
-
(2001)
Org. Lett
, vol.3
, pp. 937
-
-
Concellón, J.M.1
Bernad, P.L.2
Bardales, E.3
-
31
-
-
30144442326
-
-
Concellón, J. M.; Rodríguez-Solla, H.; Simal, C.; Huerta, M. Org. Lett. 2005, 7, 5833.
-
(2005)
Org. Lett
, vol.7
, pp. 5833
-
-
Concellón, J.M.1
Rodríguez-Solla, H.2
Simal, C.3
Huerta, M.4
-
32
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1842863015
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α-Chloroaldehydes can be easily obtained, see: Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790.
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(a) α-Chloroaldehydes can be easily obtained, see: Halland, N.; Braunton, A.; Bachmann, S.; Marigo, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 4790.
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0000921726
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α-Chlorination of α-alkylated aldehydes was carried out using sulfuryl chloride: Stevens, C. L.; Farkas, E.; Gillis, B. J. Am. Chem. Soc. 1954, 76, 2695.
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(b) α-Chlorination of α-alkylated aldehydes was carried out using sulfuryl chloride: Stevens, C. L.; Farkas, E.; Gillis, B. J. Am. Chem. Soc. 1954, 76, 2695.
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33846445199
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General Procedure for the Synthesis of Compounds 3. Trimethylsilylmethyllithium (12 mL, 1.0 M solution in pentane) was added at -85 °C to a solution of the corresponding α-chloroaldehyde 1(10 mmol) in THF (10 mL, After stirring for 2 h, the reaction mixture was quenched by addition of sat. aq NH4Cl (10 mL, Standard work-up provided crude 3-chloro-1-(trimethylsilyl)alkan-2-ols 2. The O-acetylation reaction was carried out by treatment of the corresponding crude 3-chloro-1-(trimethylsilyl) alkan-2-ols 2 (1 mmol) with Et3N (10 mL, Ac2O (10 mL) and a catalytic amount of DMAP (5 mg, The reaction mixture was stirred for 12 h at r.t, then the reaction was quenched with ice-cold H2O 30 mL, The organic material was extracted with CH2Cl2. The combined extracts were dried over Na2SO4 and the solvent was removed under reduced pressure affording compounds 3 which were utiliz
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4 and the solvent was removed under reduced pressure affording compounds 3 which were utilized without further purification. Compounds 3 were obtained as a mixture of diastereoisomers (roughly 1:1), after column chromatography (hexane-EtOAc, 5:1).
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35
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2 in THF was rapidly obtained by reaction of diiodomethane with samarium powder in the presence of sonic waves: Concellón, J. M.; Rodríguez-Solla, H.; Bardales, E.; Huerta, M. Eur. J. Org. Chem. 2003, 1775.
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2 in THF was rapidly obtained by reaction of diiodomethane with samarium powder in the presence of sonic waves: Concellón, J. M.; Rodríguez-Solla, H.; Bardales, E.; Huerta, M. Eur. J. Org. Chem. 2003, 1775.
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36
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33846453490
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General Procedure for the Synthesis of Allylsilanes 4. A solution of SmI2 (1.2 mmol) in THF (12 mL) was added dropwise, under a nitrogen atmosphere, to a stirred solution of the corresponding starting material 3 (0.4 mmol) at r.t. The reaction mixture was then refluxed for 8 h. After this time, it was quenched with aq HCl (0.1 M, 10 mL, The organic material was extracted with Et2O. The combined extracts were dried over Na2SO4 and the solvent was removed under reduced pressure affording crude compounds 4 which were purified by short-column chromatography (silica gel, pentane as eluent, Spectroscopical data for the compounds 4 which are not described in the literature are given here, Z)-Dodeca-2,11-dienyltrimethylsilane (4d, Rf= 0.83 (pentane, 1H NMR (300 MHz, CDCl3, δ, 5.80 (ddt, J, 17.0, 10.2, 6.7 Hz, 1 H, 5.40-5.32 (m, 1 H, 5.28-5.21 (m, 1 H, 4.98 dd
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-1.
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38
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0012852372
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Shiragami, H.; Kawamoto, T.; Imi, K.; Matsubara, S.; Utimoto, K.; Nozaki, H. Tetrahedron 1988, 44, 4009.
-
(1988)
Tetrahedron
, vol.44
, pp. 4009
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Shiragami, H.1
Kawamoto, T.2
Imi, K.3
Matsubara, S.4
Utimoto, K.5
Nozaki, H.6
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39
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33845281959
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Other six-membered-ring transition-state models have been proposed to explain the selectivity in other reactions of SmI2: (a) Molander, G. A, Etter, J. B, Zinke, P. W. J. Am. Chem. Soc. 1987, 109, 453
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2: (a) Molander, G. A.; Etter, J. B.; Zinke, P. W. J. Am. Chem. Soc. 1987, 109, 453.
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40
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0001272931
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(b) Urban, D.; Skrydstrup, T.; Beau, J. M. J. Org. Chem. 1998, 63, 2507.
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(1998)
J. Org. Chem
, vol.63
, pp. 2507
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Urban, D.1
Skrydstrup, T.2
Beau, J.M.3
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41
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0040184024
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Concellon, J. M.; Pérez-Andrés, J. A.; Rodríguez- Solla, H. Angew. Chem. Int. Ed. 2000, 39, 2773.
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(2000)
Angew. Chem. Int. Ed
, vol.39
, pp. 2773
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Concellon, J.M.1
Pérez-Andrés, J.A.2
Rodríguez- Solla, H.3
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42
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0035898426
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Concellón, J. M.; Pérez-Andrés, J. A.; Rodríguez-Solla, H. Chem. Eur. J. 2001, 7, 3062.
-
(2001)
Chem. Eur. J
, vol.7
, pp. 3062
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Concellón, J.M.1
Pérez-Andrés, J.A.2
Rodríguez-Solla, H.3
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44
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0002068159
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To see previous works about the γ-effect of the silicon atom, see: a
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To see previous works about the γ-effect of the silicon atom, see: (a) Sommer, L. H.; Dorfman, E.; Goldberg, G. M.; Whitmore, F. C. J. Am. Chem. Soc. 1946, 68, 488.
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(1946)
J. Am. Chem. Soc
, vol.68
, pp. 488
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Sommer, L.H.1
Dorfman, E.2
Goldberg, G.M.3
Whitmore, F.C.4
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47
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33846447358
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This is consistent with other previously reported SmI2- mediated β-elimination methodologies with Z-selectivity see ref. 7-9, So, when aryl-substituted olefins were obtained an enhancement of the E-stereoisomer was observed
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2- mediated β-elimination methodologies with Z-selectivity (see ref. 7-9). So, when aryl-substituted olefins were obtained an enhancement of the E-stereoisomer was observed.
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48
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33846443914
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An isomerization process of the Z-phenyl alkene to the more stable E-isomer cannot be discarded under this reaction conditions
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An isomerization process of the Z-phenyl alkene to the more stable E-isomer cannot be discarded under this reaction conditions.
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49
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18444385349
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2-promoted processes when benzylic radicals are generated: Davies, S. G.; Rodríguez-Solla, H.; Tamayo, J. A.; Cowley, A. R.; Concellón, C.; Garner, A. C.; Parkes, A. L.; Smith, A. D. Org. Biomol. Chem. 2005, 3, 1435.
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2-promoted processes when benzylic radicals are generated: Davies, S. G.; Rodríguez-Solla, H.; Tamayo, J. A.; Cowley, A. R.; Concellón, C.; Garner, A. C.; Parkes, A. L.; Smith, A. D. Org. Biomol. Chem. 2005, 3, 1435.
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