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0002874969
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J.D. Morrison J.W. Scott Academic Press New York
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J.W. Scott J.D. Morrison J.W. Scott Asymmetric Synthesis Vol. 4 1984 Academic Press New York 1 226
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(1984)
Asymmetric Synthesis
, vol.4
, pp. 1-226
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Scott, J.W.1
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3
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0000119097
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K. Mori Tetrahedron 45 1989 3233 3298
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(1989)
Tetrahedron
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, pp. 3233-3298
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Mori, K.1
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0343522447
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B.R. Laurence, K. Mori, T. Otsuka, J.A. Pickett, and L.J. Wadhams J. Chem. Ecol. 11 1985 643 648
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(1985)
J. Chem. Ecol.
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, pp. 643-648
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Laurence, B.R.1
Mori, K.2
Otsuka, T.3
Pickett, J.A.4
Wadhams, L.J.5
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15
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30744472594
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G. Lin, H. Xu, B. Wu, G. Guo, and W. Zhou Tetrahedron Lett. 26 1985 1233 1236
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(1985)
Tetrahedron Lett.
, vol.26
, pp. 1233-1236
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Lin, G.1
Xu, H.2
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Guo, G.4
Zhou, W.5
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27
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0028091072
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C. Gravier-Pelletier, M. Saniere, I. Charvet, Y.L. Merrer, and J.-C. Depezay Tetrahedron Lett. 35 1994 115 118
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(1994)
Tetrahedron Lett.
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Gravier-Pelletier, C.1
Saniere, M.2
Charvet, I.3
Merrer, Y.L.4
Depezay, J.-C.5
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35
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33645197901
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note
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Method A: n-Bromodecane (0.035 mol) in hexane (50 mL) was added over a period of 2 h to a stirred suspension of finely cut lithium (0.077 mol) in dry hexane (100 mL) at 10-15°C under argon. The mixture was stirred at that temperature for 3 h more when the majority of lithium had dissolved. The suspension was cooled to -40°C. To it a solution of 1 (0.01 mol) in THF (50 mL) was added over a period of 30 min. The mixture was stirred at -40°C for 1 h, at 0°C for 3 h and at room temperature overnight. It was then filtered quickly and the residue containing the unreacted lithium metal was washed with dry THF. [This excess lithium was later decomposed by treatment with cold MeOH.] The combined filtrates were treated with water and extracted with EtOAc. Solvent removal under reduced pressure and column chromatography of the residue (0-20% EtOAc in hexane) afforded 2a and 2b. Method B: n-Bromodecane (0.035 mol) in ether (50 mL) was added over a period of 3 h to a stirred suspension of finely cut lithium (0.077 mol) in dry ether (150 mL) at around -10°C under argon. The mixture was stirred at -10°C for 1 h further to dissolve the most of the lithium. The suspension was cooled to -40°C. To it, a solution of 1 (0.01 mol) in ether (50 mL) was added over a period of 30 min. The mixture was stirred at -40°C for 2 h, at -10°C for 6 h, then filtered. After a normal work up, the products were isolated as in Method A.
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39
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0007049152
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F. Sato, Y. Kabayashi, O. Takahashi, and T. Chiba J. Chem. Soc., Chem. Commun. 1985 1636 1638
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(1985)
J. Chem. Soc., Chem. Commun.
, pp. 1636-1638
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Sato, F.1
Kabayashi, Y.2
Takahashi, O.3
Chiba, T.4
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40
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33645205217
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note
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3): δ 0.86 (br t, 3H), 1.04 (s, 9H), 1.2-1.4 (m, 18H), 2.12 (dd, J = 5.4, 2.6 Hz, 1H), 2.45 (dd, J = 5.06, 3.92 Hz, 1H), 2.83-2.98 (m, 1H), 3.38 (dd, J = 11.0, 5.2 Hz, 1H), 7.39 (m, 6H), 7.64 (m, 4H).
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41
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33645207136
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note
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3): δ 0.86 (br t, 3H), 1.04 (s, 9H), 1.2-1.6 (m, 22H overlapped with s at 1.58 for 1H, OH), 1.9-2.05 (m, 2H), 3.4-3.6 (m, 2H), 5.0-5.2 (m, 2H), 5.7-5.9 (m, 1H), 7.36 (m, 6H), 7.65 (m, 4H).
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43
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33645200810
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note
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3): δ 0.86 (t, J = 7.2 Hz, 3H), 1.22 (br m, 16H), 1.4-1.95 (m, 6H), 2.05 (s, 3H), 2.3-2.6 (m, 2H), 4.29-4.32 (m, 1H), 4.9-5.0 (m, 1H).
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