New Nickel-Catalyzed Carbozincation of Alkynes: A Short Synthesis of (Z)-Tamoxifen

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 1-2, 1997, Pages 93-95

  Stüdemann, Thomas ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Alkynes; Cyclizations; Homogeneous catalysis; Tamoxifen

Indexed keywords

EID: 0030739251     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199700931     Document Type: Article

References (25)

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8. For mechanistic studies showing that olefin coordination facilitates reductive eliminations, see a) T. Yamamoto, A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1971, 93, 3350-3359; b) R. Sustmann, J. Lau, M. Zipp, Tetrahedron Lett. 1986, 27, 5207-5210; c) R. Sustman, J. Lau, Chem. Ber. 1986, 119, 2531-2541; d) R. Sustmann, J. Lau, M. Zipp, Recl. Trav. Chim. Pays-Bas 1986, 105, 356-359; e) R. Sustmann, P. Hopp, P. Holl, Tetrahedron Lett. 1989, 30, 689-692; f) R. van Asselt, C. J. Elsevier, Tetrahedron 1994, 50, 323-334.
9. For mechanistic studies showing that olefin coordination facilitates reductive eliminations, see a) T. Yamamoto, A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1971, 93, 3350-3359; b) R. Sustmann, J. Lau, M. Zipp, Tetrahedron Lett. 1986, 27, 5207-5210; c) R. Sustman, J. Lau, Chem. Ber. 1986, 119, 2531-2541; d) R. Sustmann, J. Lau, M. Zipp, Recl. Trav. Chim. Pays-Bas 1986, 105, 356-359; e) R. Sustmann, P. Hopp, P. Holl, Tetrahedron Lett. 1989, 30, 689-692; f) R. van Asselt, C. J. Elsevier, Tetrahedron 1994, 50, 323-334.
10. For mechanistic studies showing that olefin coordination facilitates reductive eliminations, see a) T. Yamamoto, A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1971, 93, 3350-3359; b) R. Sustmann, J. Lau, M. Zipp, Tetrahedron Lett. 1986, 27, 5207-5210; c) R. Sustman, J. Lau, Chem. Ber. 1986, 119, 2531-2541; d) R. Sustmann, J. Lau, M. Zipp, Recl. Trav. Chim. Pays-Bas 1986, 105, 356-359; e) R. Sustmann, P. Hopp, P. Holl, Tetrahedron Lett. 1989, 30, 689-692; f) R. van Asselt, C. J. Elsevier, Tetrahedron 1994, 50, 323-334.
11. For mechanistic studies showing that olefin coordination facilitates reductive eliminations, see a) T. Yamamoto, A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1971, 93, 3350-3359; b) R. Sustmann, J. Lau, M. Zipp, Tetrahedron Lett. 1986, 27, 5207-5210; c) R. Sustman, J. Lau, Chem. Ber. 1986, 119, 2531-2541; d) R. Sustmann, J. Lau, M. Zipp, Recl. Trav. Chim. Pays-Bas 1986, 105, 356-359; e) R. Sustmann, P. Hopp, P. Holl, Tetrahedron Lett. 1989, 30, 689-692; f) R. van Asselt, C. J. Elsevier, Tetrahedron 1994, 50, 323-334.
12. For mechanistic studies showing that olefin coordination facilitates reductive eliminations, see a) T. Yamamoto, A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1971, 93, 3350-3359; b) R. Sustmann, J. Lau, M. Zipp, Tetrahedron Lett. 1986, 27, 5207-5210; c) R. Sustman, J. Lau, Chem. Ber. 1986, 119, 2531-2541; d) R. Sustmann, J. Lau, M. Zipp, Recl. Trav. Chim. Pays-Bas 1986, 105, 356-359; e) R. Sustmann, P. Hopp, P. Holl, Tetrahedron Lett. 1989, 30, 689-692; f) R. van Asselt, C. J. Elsevier, Tetrahedron 1994, 50, 323-334.
13. For mechanistic studies showing that olefin coordination facilitates reductive eliminations, see a) T. Yamamoto, A. Yamamoto, S. Ikeda, J. Am. Chem. Soc. 1971, 93, 3350-3359; b) R. Sustmann, J. Lau, M. Zipp, Tetrahedron Lett. 1986, 27, 5207-5210; c) R. Sustman, J. Lau, Chem. Ber. 1986, 119, 2531-2541; d) R. Sustmann, J. Lau, M. Zipp, Recl. Trav. Chim. Pays-Bas 1986, 105, 356-359; e) R. Sustmann, P. Hopp, P. Holl, Tetrahedron Lett. 1989, 30, 689-692; f) R. van Asselt, C. J. Elsevier, Tetrahedron 1994, 50, 323-334.
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16. a) For a zirconiumu(IV)-catalyzed carbozincation of alkynes see E. Negishi, D. E. Van Horn, T. Yoshida, C. L. Rand, Organometallics 1983, 2, 563-565; b) B. B. Snider, R. S. E. Conn, M. Karras, Tetrahedron Lett. 1979, 1679-1682.
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18. Methylcuprates undergo addition to alkynes only with difficulty: P. Knochel in Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon, 1991, pp. 865-912; good results could be achieved only by using zirconium-mediated carboalumination: E. Negishi, D. E. Van Horn, T. Yoshida, J. Am. Chem. Soc. 1985, 107, 6639-6647.
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