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(a) Hosokawa, T.; Murahashi, S.-I. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2; Negishi, E.-i., Ed.; John Wiley and Sons: New York, 2002, 2141-2192.
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(b) See also: Fugami, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 2050.
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In this report, we use the term of stereospecificity as a classical sense, see: Ward, R. S. Chem. Br. 1991, 803.
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Chem. Br.
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Ward, R.S.1
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19
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33751277203
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note
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3): δ = 1.20 (t, J = 7.2 Hz, 3 H), 2.84 (d, J = 16.8 Hz, 1 H), 2.91-2.98 (dm, 1 H), 3.50 (dq, J = 7.2 Hz, 1 H), 3.78 (dq, J = 7.2 Hz, 1 H), 4.54 (d, J = 12.8 Hz, 1 H), 4.63 (d, J = 12.8 Hz, 1 H), 5.36 (d, J = 5.2 Hz, 1 H), 6.38 (s, 1 H), 7.18-7.36 (m, 5 H).
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20
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33751291174
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note
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NOE correlation of vinyl proton (δ = 6.42 ppm) in (Z)-4 was observed with one of C-3 protons (δ = 2.70 ppm), suggesting that these protons are proximal to each other, but not with C-5 protons. On the other hand, vinyl proton (δ = 6.38 ppm) in (E)-5 correlates with one of C-5 protons (δ = 4.54 ppm), but not with C-3 protons (Figure 3). (Diagram presented)
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21
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25944466707
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Negishi, E.-i., Ed.; John Wiley and Sons: New York
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(a) Bräse, S.; de Meijere, A. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1; Negishi, E.-i., Ed.; John Wiley and Sons: New York, 2002, 1123-1178.
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Bräse, S.1
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and references cited therein
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(b) Bäckvall, J.-E.; Hopkins, R. B.; Grennberg, H.; Mader, M. M.; Awasthi, A. K. J. Am. Chem. Soc. 1990, 112, 5160; and references cited therein.
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Ref. 5e.
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Ref. 5e.
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31
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0033555630
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and references cited therein
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(b) Berreau, L. M.; Mahapatra, S.; Halfen, J. A.; Houser, R. P.; Young, V. G. Jr.; Tolman, W. B. Angew. Chem. Int. Ed. 1999, 38, 207; and references cited therein.
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Tolman, W.B.6
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and also references cited therein
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(c) Kodera, M.; Kawata, T.; Kano, K.; Tachi, Y.; Ito, S.; Kojo, S. Bull. Chem. Soc. Jpn. 2003, 76, 1957; and also references cited therein.
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33
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33751266270
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note
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2 (balloon) at r.t. gave quinone 10 in ca. 98% yield (GC). For the survey of these points, the use of catechol itself, instead of 11, was not successful, because the analysis of o-quinone was difficult because of its instability.
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34
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2, see: (a) Mueller, J. A.; Goller, C. P.; Sigman, M. S. J. Am. Chem. Soc. 2004, 126, 9724.
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(b) See also: Steinhoff, B. A.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 11268. Although such a catalysis is not necessarily ruled out in the present case, it seems to be difficult to accommodate the observed effect of catechol or quinone into it.
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Steinhoff, B.A.1
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(c) Denney, M. C.; Smythe, N. A.; Cetto, K. L.; Kemp, R. A.; Goldberg, K. I. J. Am. Chem. Soc. 2006, 128, 2508.
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39
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33751304401
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note
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2 (balloon). After the mixture was stirred for 0.5 h at r.t. (aging time of catalyst), ethyl vinyl ether (1442 mg, 20 mmol) was added to the flask, and a solution of (E)-3-phenyl-2-propen-1-ol (670 mg, 5.0 mmol) in MeCN (2.5 mL) was then added. The reaction mixture was stirred for 7 h at r.t. In order to determine GC yield of 4, tetraethylene glycol dimethyl ether (63.43 mg) was added to the flask as an internal standard. The GC analysis showed that 82% yield of 4 was formed. This mixture was subjected to purification on a Florisil column (3 g, 10 mm × 80 mm) with elution of EtOAc-n-hexane (1:20, 100 mL), and evaporation of solvent gave 4 (990 mg, 78%) as nearly pure state. (17) Isolation of 2-ethoxy-4-exomethylenetetrahydrofuran derived from 3a was rather difficult because of its lower boiling point, and thus butyl vinyl ether (3b) was used in these experiments.
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40
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0141856236
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(a) de Vries, A. H. M.; Mulders, J. M. C. A.; Mommers, J. H. M.; Henderickx, H. J. W.; de Vries, J. G. Org. Lett. 2003, 5, 3285.
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(d) See also: Komano, T.; Iwasawa, T.; Tokunaga, M.; Obora, Y.; Tsuji, Y. Org. Lett. 2005, 7, 4677.
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