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(b) Molander, G. A. In Organic Reactions, L. A. Paquette, Ed.; John Wiley & Sons: New York, 1994; Vol. 46; pp 211-367.
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(c) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195-1196.
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(g) Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265-1276.
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(h) Kito, M.; Sakai, T.; Shirahama, H.; Miyashita, M.; Matsuda, F. Synlett 1997, 1997, 219-220.
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(b) Inanaga, J.; Tabuchi, T.; Yamaguchi, M. Chem. Express 1991, 6, 419-422.
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(c) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Kidorui 1991, 18, 144-145.
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(e) Sugimoto, Y.; Hanamoto, T.; Inanaga, J. Appl. Organometal. Chem. 1995, 9, 369-375.
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(f) Mikami, K.; Yoshida, A.; Matsumoto, S.; Feng, F.; Matsumoto, Y.; Sugino, A.; Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1995, 36, 907-908.
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5. Recent applications: (a) Alexakis, A.; Marek, I.; Mangeney, P.; Normant, J. F. Tetrahedron 1991, 47, 1677-1696.
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(c) Hou, Z. M.; Zhang, Y. G.; Wakatsuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149-153.
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8. (a) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3891-3894.
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(b) Matsukawa, M.; Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 2101-2102.
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(c) Bonini, C.; Federici, C.; Rossi, L.; Righi, G. J. Org. Chem. 1995, 60, 4803-4812.
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0010579050
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Formation of the enynes probably takes place by ring-opening of epoxides with iodide anion associated to Sm(III), followed by reduction of the corresponding iodohydrins (i.e. 3d): See ref's 2a, 8a,b
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9. Formation of the enynes probably takes place by ring-opening of epoxides with iodide anion associated to Sm(III), followed by reduction of the corresponding iodohydrins (i.e. 3d): See ref's 2a, 8a,b.
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36
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84945959007
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10. The use of Sm(III) species in aldol reactions has been reported: (a) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420.
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Sasai, H.1
Suzuki, T.2
Arai, S.3
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Shibasaki, M.5
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(d) Sasai, H.; Arai, S.; Shibasaki, M. J. Org. Chem. 1994, 59, 2661-2664.
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Arai, S.2
Shibasaki, M.3
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11. Souppe, J.; Danon, L.; Namy, J. L.; Kagan, H. B. J. Organomet. Chem. 1983, 250, 227-236.
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Kagan, H.B.4
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12. The migration of silyl groups between adjacent hydroxyl groups has been shown to proceed under basic conditions: (a) Mulzer, J.; Schöllhorn, B. Angew. Chem. Int. Ed. Engl. 1990, 29, 431-432.
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Mulzer, J.1
Schöllhorn, B.2
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43
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33845280764
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13. A related SET from Ti(III) species to epoxides yielding α-alkoxy radicals has been reported: Nugent, W. A.; RajanBabu, T. V. J. Am. Chem. Soc. 1988, 110, 8561-8562.
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Nugent, W.A.1
Rajanbabu, T.V.2
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44
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0000627957
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and references cited therein
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14. See for example: Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418-7429, and references cited therein.
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Molander, G.A.1
Harris, C.R.2
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85022594998
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15. The coexistence of radical and organometallic pathways in SmI2-promoted couplings has been demonstrated: Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943-961.
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(1992)
Synlett
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Totleben, M.J.4
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37049122182
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16. Hlubucek, J. R.; Hora, J.; Russell, S. W.; Toube, T. P.; Weedon, B. C. L. J. Chem. Soc., Perkin Trans. 1 1974, 848-852.
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Weedon, B.C.L.5
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47
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0010541299
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5e,18,19 cycloisomerization of diols 2a, d, j further confirmed these stereochemical assignments. See Ref. 6 and following paper in this issue
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5e,18,19 cycloisomerization of diols 2a, d, j further confirmed these stereochemical assignments. See Ref. 6 and following paper in this issue.
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50
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0002714675
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20. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
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0010543464
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5a for the preparation of 1b was modified as follows: THF was used as solvent and n-BuLi at -78°C as base
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5a for the preparation of 1b was modified as follows: THF was used as solvent and n-BuLi at -78°C as base.
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53
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0000910413
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Purification by distillation, as reported, resulted in isomerization to oct-2-en-2-yl inflate. Alternatively, flash chromatography in hexanes afforded a 93:7 mixture of oct-1-en-2-yl triflate and its isomeric internal triflate
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23. Takai, K.; Sakogawa, K.; Kataoka, Y.; Oshima, K.; Utimoto, K. Org. Synth. 1993, 72, 180-188. Purification by distillation, as reported, resulted in isomerization to oct-2-en-2-yl inflate. Alternatively, flash chromatography in hexanes afforded a 93:7 mixture of oct-1-en-2-yl triflate and its isomeric internal triflate.
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(1993)
Org. Synth.
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Takai, K.1
Sakogawa, K.2
Kataoka, Y.3
Oshima, K.4
Utimoto, K.5
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54
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0000387501
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24. Seyferth, D.; Heeren, J. K.; Singh, G. J. Organometal. Chem. 1966, 5, 267-274.
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84987190612
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25. Schmidt, U.; Respondek, M.; Lieberknecht, A.; Werner, J.; Fischer, P. Synthesis 1989, 256-261.
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Synthesis
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Schmidt, U.1
Respondek, M.2
Lieberknecht, A.3
Werner, J.4
Fischer, P.5
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56
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0010611975
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note
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2, should be kept at about 2-3 mol% as the use of larger excesses in reactions of 1a was observed to lead occasionally to the formation of diene byproducts i and to loss of diastereoselectivity in the formation of diols 2. (formula presented)
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57
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27. Molander, G. A.; Etter, J. B.; Zinke, P. W. J. Am. Chem. Soc. 1987, 109, 453-463.
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Molander, G.A.1
Etter, J.B.2
Zinke, P.W.3
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