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84988080205
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In a recent paper, the synthesis of similar bi- and tricyclic systems with a protected glycin instead of a malonic ester moiety by a reductive palladium-catalyzed cyclization of 2,6-dibromo-1,6-dienes according to Grigg and subsequent Diels-Alder reaction performed in two steps was described
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10. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 2033-2048. In a recent paper, the synthesis of similar bi- and tricyclic systems with a protected glycin instead of a malonic ester moiety by a reductive palladium-catalyzed cyclization of 2,6-dibromo-1,6-dienes according to Grigg and subsequent Diels-Alder reaction performed in two steps was described: Moreno-Mañas, M.; Pleixats, R.; Roglans, A. Liebigs Ann. Chem. 1995, 1807-1814.
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85030277645
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6
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6
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41
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0001393289
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31. Reactions with similar iodides and triflates are known, see e. g.: Larock, R. C.; Song, H; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919-2922.
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The unsubstituted parent of 70, dicyclopropylideneethane, has been reported and used in Diels-Alder reactions
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32. The unsubstituted parent of 70, dicyclopropylideneethane, has been reported and used in Diels-Alder reactions: Paquette, L. A.; Wells, G. J.; Wickham, G. J. Org. Chem. 1984, 49, 3618-3621.
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33. Fournet, G.; Balme, G.; Barieux, J. J.; Gore, J. Tetrahedron 1988, 44, 5821-5832.
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34. Larock, R. C.; Varaprath, S. J. Org. Chem. 1984, 49, 3432-3435. Grigg, R.; Kennewell, P.; Teasdale, A; Sridharan, V. Tetrahedron Lett. 1993, 34, 153-156.
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38. For the synthesis of (cyclopropylidenethyl)malonates see: Stolle, A.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1990, 31, 4593-4596. Stolle, A.; Salaün, J.; de Meijere, A. Synlett 1991, 327-330. Stolle, A.; Ollivier, J.; Piras, P. P.; Salaün, J.; de Meijere, A. J. Am. Chem. Soc. 1992, 114, 4051-4067.
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38. For the synthesis of (cyclopropylidenethyl)malonates see: Stolle, A.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1990, 31, 4593-4596. Stolle, A.; Salaün, J.; de Meijere, A. Synlett 1991, 327-330. Stolle, A.; Ollivier, J.; Piras, P. P.; Salaün, J.; de Meijere, A. J. Am. Chem. Soc. 1992, 114, 4051-4067.
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38. For the synthesis of (cyclopropylidenethyl)malonates see: Stolle, A.; Salaün, J.; de Meijere, A. Tetrahedron Lett. 1990, 31, 4593-4596. Stolle, A.; Salaün, J.; de Meijere, A. Synlett 1991, 327-330. Stolle, A.; Ollivier, J.; Piras, P. P.; Salaün, J.; de Meijere, A. J. Am. Chem. Soc. 1992, 114, 4051-4067.
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39. For reports on favorable effects with the use of silver salts in Heck reactions see: Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 51, 5286-5290. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
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39. For reports on favorable effects with the use of silver salts in Heck reactions see: Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 51, 5286-5290. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
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39. For reports on favorable effects with the use of silver salts in Heck reactions see: Karabelas, K.; Hallberg, A. J. Org. Chem. 1986, 51, 5286-5290. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
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Trost et al. mentioned briefly (footnote 10) that the isomerization of (Z)-56 to 59 was catalyzed by Pd(II); however, no details were given
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85030276358
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The reasons for this change in regioselectivity are not obvious. It might be interesting to approach a better understanding by MO calculations
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43. The reasons for this change in regioselectivity are not obvious. It might be interesting to approach a better understanding by MO calculations.
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