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Volumn 62, Issue 12, 1997, Pages 3994-4001

Complexation of Vinylcyclopropanes with Zirconocene - 1-butene Complex: Application to the Stereocontrolled Synthesis of Steroidal Side Chains

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EID: 0000751817     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962064r     Document Type: Article
Times cited : (29)

References (92)
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    • (1994) J. Organomet. Chem. , vol.471 , pp. 1
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
    • (1976) J. Organomet. Chem. , vol.117 , pp. 245
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    • Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York
    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 899
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
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    • Doyle, M.P.1    Van Leusen, D.2
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
    • (1982) J. Org. Chem. , vol.47 , pp. 5326
    • Doyle, M.P.1    Van Leusen, D.2
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
    • (1980) J. Org. Chem. , vol.45 , pp. 5020
    • Hudlicky, T.1    Koszyk, F.J.2    Kutchan, T.M.3    Sheth, J.P.4
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 153
    • Hiroi, K.1    Arinaga, Y.2
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
    • (1979) Chem. Lett. , pp. 927
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 2871
    • Morizawa, Y.1    Oshima, K.2    Nozaki, H.3
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
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    • For reviews and lead references, see: (a) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720. (b) Khusuntdinov, R. I.; Dzhemilev, U. M. J. Organomet. Chem. 1994, 471, 1. (c) Aumann, R.; Averbeck, H. J. Organomet. Chem. 1978, 160, 241. (d) Salzer, A. J. Organomet. Chem. 1976, 117, 245. (e) Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991; Vol. 5, p 899. (f) Doyle, M. P.; van Leusen, D. J. Am. Chem. Soc. 1981, 103, 5917. (g) Doyle, M. P.; van Leusen, D. J. Org. Chem. 1982, 47, 5326. (h) Hudlicky, T.; Koszyk, F. J.; Kutchan, T. M.; Sheth, J. P. J. Org. Chem. 1980, 45, 5020. (i) Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (j) Murakami, M.; Nishida, S. Chem. Lett. 1979, 927. (k) Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 2871. (l) Grimme, W. Chem. Ber. 1967, 100, 113. (m) Liotta, F. J., Jr.; Carpenter, B. K. J. Am. Chem. Soc. 1985, 107, 6426.
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    • note
    • 3. A total of 3032 unique reflections were collected. The final R factor was 0.064. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
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    • For recent reviews, see: (a) Charette, A. B.; Marcoux, J.-F. Synlett 1995, 1197. (b) Motherwell, W. B.; Nutley, C. J. Contemp. Org. Synth. 1994, 1, 219 and the references cited therein.
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    • Motherwell, W.B.1    Nutley, C.J.2


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