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Volumn 7, Issue 5, 2005, Pages 909-911

Stereoselective synthesis of multisubstituted alkenes via conformationally labile alkenyllithium species

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALLYL COMPOUND; CARBON; COPPER; HALIDE; LITHIUM DERIVATIVE; PALLADIUM; SILICON;

EID: 15044356699     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050114l     Document Type: Article
Times cited : (18)

References (48)
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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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    • (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.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 3228
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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.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10221
    • Shirakawa, E.1    Yamasaki, K.2    Yoshida, H.3    Hiyama, T.4
  • 16
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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.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2931
    • Urabe, H.1    Hamada, T.2    Sato, F.3
  • 17
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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.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 627
    • Ramachandran, P.V.1    Reddy, M.V.R.2    Rudd, M.T.3
  • 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.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 93
    • 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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    • (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.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 10386
    • Denmark, S.E.1    Amburgey, J.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.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6840
    • Shindo, M.1    Matsumoto, K.2    Mori, S.3    Shishido, K.4
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    • and references therein
    • Our interest in organotellurium compounds in organic synthesis: (a) Yamago, S. Synlett 2004, 1875, and references therein. (b) Yamago, S.; Miyoshi, M.; Miyazoe, H.; Yoshida, J. Angew. Chem., Int. Ed. 2002, 41, 1407. (c) Yamago, S.; Kokubo, K.; Hara, O.; Masuda, S.; Yoshida, J. J. Org. Chem. 2002, 67, 8584.
    • (2004) Synlett , pp. 1875
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    • Our interest in organotellurium compounds in organic synthesis: (a) Yamago, S. Synlett 2004, 1875, and references therein. (b) Yamago, S.; Miyoshi, M.; Miyazoe, H.; Yoshida, J. Angew. Chem., Int. Ed. 2002, 41, 1407. (c) Yamago, S.; Kokubo, K.; Hara, O.; Masuda, S.; Yoshida, J. J. Org. Chem. 2002, 67, 8584.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1407
    • Yamago, S.1    Miyoshi, M.2    Miyazoe, H.3    Yoshida, J.4
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    • Our interest in organotellurium compounds in organic synthesis: (a) Yamago, S. Synlett 2004, 1875, and references therein. (b) Yamago, S.; Miyoshi, M.; Miyazoe, H.; Yoshida, J. Angew. Chem., Int. Ed. 2002, 41, 1407. (c) Yamago, S.; Kokubo, K.; Hara, O.; Masuda, S.; Yoshida, J. J. Org. Chem. 2002, 67, 8584.
    • (2002) J. Org. Chem. , vol.67 , pp. 8584
    • Yamago, S.1    Kokubo, K.2    Hara, O.3    Masuda, S.4    Yoshida, J.5
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    • Wilkinson, G., Stones, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, UK
    • (a) Wardell, J. L. In Comprehensive Organometallic Chemistry, Wilkinson, G., Stones, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, UK, 1982; Vol. 1, pp 42-120.
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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
    • 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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