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In Symposium-in Print
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For recent reviews: (a) Marek, I., Ed. Titanium and Zirconium in Organic Synthesis; Wiley-VCH: Germany, 2002 (b) Suzuki, K., Wipf, P., Eds. Recent Advances in the Chemistry of Zirconocenes. In Symposium-in Print. Tetrahedron 2004, 60, 1267. (c) Wipf, P.; Jahn, H., Tetrahedron 1996, 52, 12853 and references cited therein.
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For recent reviews: (a) Marek, I., Ed. Titanium and Zirconium in Organic Synthesis; Wiley-VCH: Germany, 2002 (b) Suzuki, K., Wipf, P., Eds. Recent Advances in the Chemistry of Zirconocenes. In Symposium-in Print. Tetrahedron 2004, 60, 1267. (c) Wipf, P.; Jahn, H., Tetrahedron 1996, 52, 12853 and references cited therein.
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To the best of our knowledge, the Li species is unknown. Although corresponding Mg species are known in several examples, the use of 2-vinylbenzylmagnesium species has been limited mostly to polymer chemistry, (a) Hatada, K.; Shiozaki, T.; Ute, K.; Kitayama, T. Polymer Bull. 1988, 19, 231. (b) Kuendig, E. P.; Perret, C. Helv. Chim. Acta 1981, 64, 2606. (c) Duboudin, J. G.; Jousseaume, B.; Pinet, M. J. Chem. Soc., Chem. Commun. 1977, 454.
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To the best of our knowledge, the Li species is unknown. Although corresponding Mg species are known in several examples, the use of 2-vinylbenzylmagnesium species has been limited mostly to polymer chemistry, (a) Hatada, K.; Shiozaki, T.; Ute, K.; Kitayama, T. Polymer Bull. 1988, 19, 231. (b) Kuendig, E. P.; Perret, C. Helv. Chim. Acta 1981, 64, 2606. (c) Duboudin, J. G.; Jousseaume, B.; Pinet, M. J. Chem. Soc., Chem. Commun. 1977, 454.
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Organozirconium-mediated allylations, see.: (a) Venanzi, L. M.; Lehmann, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (b) Heron, N. M.; Adams, J. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 6205. (c) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183.
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Organozirconium-mediated allylations, see.: (a) Venanzi, L. M.; Lehmann, R.; Keil, R.; Lipshutz, B. H. Tetrahedron Lett. 1992, 33, 5857. (b) Heron, N. M.; Adams, J. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 6205. (c) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183.
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85068954328
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note
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Reaction of vinyl chloride derivative 4d with sodium amide (4 equiv, THF-HMPA) or LDA (2 equiv, THF) gave a trace or a small amount of the desired ene-yne product 10.
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-
-
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20
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2442536129
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For recent examples on total synthesis of estrone using Dane's diene, see: (a) Hu, Q. Y.; Rege, P. D.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 5984. (b) Tsogoeva, S. B.; Durner, G.; Bolte, M.; Gobel, M. Eur. J. Org. Chem. 2003, 1661. (c) Tanaka, K.; Nakashima, H.; Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 1915.
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For recent examples on total synthesis of estrone using Dane's diene, see: (a) Hu, Q. Y.; Rege, P. D.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 5984. (b) Tsogoeva, S. B.; Durner, G.; Bolte, M.; Gobel, M. Eur. J. Org. Chem. 2003, 1661. (c) Tanaka, K.; Nakashima, H.; Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 1915.
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Tsogoeva, S.B.1
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Gobel, M.4
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22
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0006114926
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For recent examples on total synthesis of estrone using Dane's diene, see: (a) Hu, Q. Y.; Rege, P. D.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 5984. (b) Tsogoeva, S. B.; Durner, G.; Bolte, M.; Gobel, M. Eur. J. Org. Chem. 2003, 1661. (c) Tanaka, K.; Nakashima, H.; Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 1915.
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Tanaka, K.1
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1842483218
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For recent reviews on enyne metathesis, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317. (b) Poulsen, C, S.; Madsen, R. Synthesis 2003, 1. (c) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
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For recent reviews on enyne metathesis, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317. (b) Poulsen, C, S.; Madsen, R. Synthesis 2003, 1. (c) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
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Synthesis
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Poulsen, C.S.1
Madsen, R.2
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1842483218
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For recent reviews on enyne metathesis, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317. (b) Poulsen, C, S.; Madsen, R. Synthesis 2003, 1. (c) Mori, M. Top. Organomet. Chem. 1998, 1, 133.
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For reviews on olefin metathesis, see: (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (f) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (h) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
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For reviews on olefin metathesis, see: (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (f) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (h) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
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Blechert, S.2
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For reviews on olefin metathesis, see: (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (f) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (h) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
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For reviews on olefin metathesis, see: (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (e) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900. (f) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371. (h) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
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For recent examples on intramolecular enyne metathesis, see: (i) Hansen, E. C.; Lee, D. Org. Lett. 2004, 6, 2035. (j) Brenneman, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (k) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2003, 125, 9582. (1) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (m) Mori, M.; Kitamura, T.; Sakakibara, N.; Sato, Y. Org. Lett. 2000, 2, 543. (n) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465.
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For recent examples on intramolecular enyne metathesis, see: (i) Hansen, E. C.; Lee, D. Org. Lett. 2004, 6, 2035. (j) Brenneman, J. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. (k) Hansen, E. C.; Lee, D. J. Am. Chem. Soc. 2003, 125, 9582. (1) Kitamura, T.; Mori, M. Org. Lett. 2001, 3, 1161. (m) Mori, M.; Kitamura, T.; Sakakibara, N.; Sato, Y. Org. Lett. 2000, 2, 543. (n) Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465.
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