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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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Kennedy, J.W.1
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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14
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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Xi, C.2
Ura, Y.3
Nakajima, K.4
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15
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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Shirakawa, E.1
Yamasaki, K.2
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Hiyama, T.4
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16
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0033620430
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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Urabe, H.1
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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Ramachandran, P.V.1
Reddy, M.V.R.2
Rudd, M.T.3
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18
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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Stüdemann, T.1
Knochel, P.2
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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Ikeda, S.1
Kondo, K.2
Sato, Y.3
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(b) Carbometalation route: Kennedy, J. W.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898. (c) Itami, K.; Nokami, T.; Ishimura, Y.; Matsudo, T.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 11577. (d) Yamanoi, S.; Seki, K.; Matsumono, T.; Suzuki, K. J. Organomet. Chem. 2001, 624, 143. (e) Takahashi, T.; Xi, C.; Ura, Y.; Nakajima, K. J. Am. Chem. Soc. 2000, 122, 3228. (f) Shirakawa, E.; Yamasaki, K.; Yoshida, H.; Hiyama, T. J. Am. Chem. Soc. 1999, 121, 10221. (g) Urabe, H.; Hamada, T.; Sato, F. J. Am. Chem. Soc. 1999, 121, 2931. (h) Ramachandran, P. V.; Reddy, M. V. R.; Rudd, M. T.; Tetrahedron Lett. 1999, 40, 627. (i) Stüdemann, T.; Knochel, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 93. (j) Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248. (k) Brown, S. D.; Armstrong, A. W. J. Am. Chem. Soc. 1996, 118, 6331. (l) Wittig reaction route: Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386. (m) Other routes: Shindo, M.; Matsumoto, K.; Mori, S.; Shishido, K. J. Am. Chem. Soc. 2002, 124, 6840.
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Tetrasubstituted alkenyltellurides were prepared from easily available enals bearing phenyltellanyl moiety. See: (a) Prim, D.; Fuss, A.; Kirsh, G.; Silva, A. M. J. Chem. Soc., Perkin Trans. 2 1999, 1175. (b) Minkin, V. I.; Sadekov, I. D.; Rivkin, B. B.; Zakharov, A. V.; Nivorozhkin, V. L.; Kompan, O. E.; Struchkov, Y. T. J. Organomet. Chem. 1997, 536, 233.
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note
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An alternative mechanism, in which the stereochemistry is determined by selective hydrolysis of pentavalent cyclic silicate intermediate, could not be rigorously ruled out.
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