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Volumn 61, Issue 8, 1996, Pages 2699-2708

New cobalt-catalyzed cycloisomerization of ε-acetylenic β-keto esters. Application to a powerful cyclization reactions cascade

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EID: 0001560416     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9600619     Document Type: Article
Times cited : (89)

References (69)
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    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
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    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
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    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 791-792
    • Trost, B.M.1    Shi, Y.2
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    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3253-3256
    • Negishi, E.-I.1    Harring, L.S.2    Owczarczyk, Z.3    Mohamud, M.M.4    Ay, M.5
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    • 0027077907 scopus 로고
    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 8039-8042
    • Meyer, F.E.1    Henniges, H.2    De Meijere, A.3
  • 7
    • 0000945674 scopus 로고
    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 773-774
    • Takacs, J.M.1    Zhu, J.2    Chandramouli, S.3
  • 8
    • 0027495588 scopus 로고
    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
    • (1993) J. Org. Chem. , vol.58 , pp. 5304-5306
    • Kucera, D.J.1    O'Connor, S.J.2    Overman, L.E.3
  • 9
    • 0027475449 scopus 로고
    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 157-160
    • Brown, S.1    Clarkson, S.2    Grigg, R.3    Sridharan, V.4
  • 10
    • 0027771099 scopus 로고
    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 8233-8236
    • Trost, B.M.1    Gelling, O.J.2
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    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
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    • Trost, B.M.1    Czeskis, B.A.2
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    • For Pd-catalyzed cycloisomerizations, see: (a) Trost. B. M Acc. Chem. Res. 1990, 23, 34-42. (b) Trost, B. M. Janssen Chim. Acta 1991, 9, 3-9. (c) Trost, B. M.; Pfrengle, W.; Urabe, H.; Dumas, J. J. Am. Chem. Soc. 1992, 114, 1923-1924. (d) Trost, B. M.; Shi, Y. Ibid. 1992, 114, 791-792. (e) Negishi, E.-I.; Harring, L. S.; Owczarczyk, Z.; Mohamud, M. M.; Ay, M. Tetrahedron Lett. 1992, 33, 3253-3256. (f) Meyer, F. E.; Henniges, H.; de Meijere, A. Ibid. 1992, 33, 8039-8042. (g) Takacs, J M.; Zhu, J.; Chandramouli, S. J. Am. Chem. Soc. 1992, 114, 773-774. (h) Kucera, D. J.; O'Connor, S. J.; Overman, L. E. J. Org. Chem. 1993, 58, 5304-5306. (i) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160. (J) Trost, B. M.; Gelling, O. J. Ibid. 1993, 34, 8233-8236. (k) Trost, B. M.; Czeskis, B. A. Ibid. 1994, 35, 211-214. (l) Takacs, J. M.; Chandramouli, S. V. Ibid. 1994, 35, 9165-9168.
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    • Takacs, J.M.1    Chandramouli, S.V.2
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    • For Rh-catalyzed cyclizations, see: Grigg, R.; Scott, R.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1988, 1357-1364 For Fecatalyzed version, see: (a) Takacs, J. M.; Weidner, J. J.; Takacs, B. E. Tetrahedron Lett. 1993, 34, 6219-6222. (b) Takacs, J. M.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942. For Zrcatalyzed version (a) Negishi E.-I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. (b) Agnel, G. Negishi, E.-I. J. Am. Chem. Soc. 1991, 113, 7424-7426. For Ni-catalyzed version, see: Tamao, K; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546.
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    • For Rh-catalyzed cyclizations, see: Grigg, R.; Scott, R.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1988, 1357-1364 For Fecatalyzed version, see: (a) Takacs, J. M.; Weidner, J. J.; Takacs, B. E. Tetrahedron Lett. 1993, 34, 6219-6222. (b) Takacs, J. M.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942. For Zrcatalyzed version (a) Negishi E.-I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. (b) Agnel, G. Negishi, E.-I. J. Am. Chem. Soc. 1991, 113, 7424-7426. For Ni-catalyzed version, see: Tamao, K; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6219-6222
    • Takacs, J.M.1    Weidner, J.J.2    Takacs, B.E.3
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    • Takacs, J.M.1    Myoung, Y.-C.2    Anderson, L.G.3
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    • Trost, B. M., Fleming, L, Paquette, L. A., Eds.; Pergamon Press: Oxford
    • For Rh-catalyzed cyclizations, see: Grigg, R.; Scott, R.; Stevenson, R. J. Chem. Soc., Perkin Trans. 1 1988, 1357-1364 For Fecatalyzed version, see: (a) Takacs, J. M.; Weidner, J. J.; Takacs, B. E. Tetrahedron Lett. 1993, 34, 6219-6222. (b) Takacs, J. M.; Myoung, Y.-C.; Anderson, L. G. J. Org. Chem. 1994, 59, 6928-6942. For Zrcatalyzed version (a) Negishi E.-I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. (b) Agnel, G. Negishi, E.-I. J. Am. Chem. Soc. 1991, 113, 7424-7426. For Ni-catalyzed version, see: Tamao, K; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546.
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    • Negishi, E.-I.1
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    • 2 had no effect.
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    • The configuration of the cycloadducts was assigned by NOE experiments: see reference 9.
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    • note
    • The authors have already deposited the atomic coordinates of 34 with the Cambridge Crystallographic Data Center: see reference 14.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.