New and efficient catalytic route to bicyclo[3.3.0]octa-1,5-dien-3-ones

Organometallics

Volumn 15, Issue 24, 1996, Pages 5191-5195

  Ojima, Iwao ^a   Kass, Dora Fracchiolla ^a   Zhu, Jiawang ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000828708     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960471n     Document Type: Article

References (32)

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13. For contributions from other laboratories, see: (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332. (b) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120. (c) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431. (d) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 33, 5799. (e) Doyle, M. P.; Shanklin, M. S. Organometallics 1993, 12, 11. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081. (g) Wright, M. E.; Cochran, B. B. J. Am. Chem. Soc. 1993, 115, 2059. (h) Zhou, J. Q.; Alper, H. Organometallics 1994, 13, 1586. (i) Monteil, F.; Matsuda, I.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4419.
14. For contributions from other laboratories, see: (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332. (b) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120. (c) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431. (d) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 33, 5799. (e) Doyle, M. P.; Shanklin, M. S. Organometallics 1993, 12, 11. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081. (g) Wright, M. E.; Cochran, B. B. J. Am. Chem. Soc. 1993, 115, 2059. (h) Zhou, J. Q.; Alper, H. Organometallics 1994, 13, 1586. (i) Monteil, F.; Matsuda, I.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4419.
15. For contributions from other laboratories, see: (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332. (b) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120. (c) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431. (d) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 33, 5799. (e) Doyle, M. P.; Shanklin, M. S. Organometallics 1993, 12, 11. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081. (g) Wright, M. E.; Cochran, B. B. J. Am. Chem. Soc. 1993, 115, 2059. (h) Zhou, J. Q.; Alper, H. Organometallics 1994, 13, 1586. (i) Monteil, F.; Matsuda, I.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4419.
16. For contributions from other laboratories, see: (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332. (b) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120. (c) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431. (d) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 33, 5799. (e) Doyle, M. P.; Shanklin, M. S. Organometallics 1993, 12, 11. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081. (g) Wright, M. E.; Cochran, B. B. J. Am. Chem. Soc. 1993, 115, 2059. (h) Zhou, J. Q.; Alper, H. Organometallics 1994, 13, 1586. (i) Monteil, F.; Matsuda, I.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4419.
17. For contributions from other laboratories, see: (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332. (b) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120. (c) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431. (d) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 33, 5799. (e) Doyle, M. P.; Shanklin, M. S. Organometallics 1993, 12, 11. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081. (g) Wright, M. E.; Cochran, B. B. J. Am. Chem. Soc. 1993, 115, 2059. (h) Zhou, J. Q.; Alper, H. Organometallics 1994, 13, 1586. (i) Monteil, F.; Matsuda, I.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4419.
18. For contributions from other laboratories, see: (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332. (b) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120. (c) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431. (d) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 33, 5799. (e) Doyle, M. P.; Shanklin, M. S. Organometallics 1993, 12, 11. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081. (g) Wright, M. E.; Cochran, B. B. J. Am. Chem. Soc. 1993, 115, 2059. (h) Zhou, J. Q.; Alper, H. Organometallics 1994, 13, 1586. (i) Monteil, F.; Matsuda, I.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4419.
19. For contributions from other laboratories, see: (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332. (b) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120. (c) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431. (d) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 33, 5799. (e) Doyle, M. P.; Shanklin, M. S. Organometallics 1993, 12, 11. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081. (g) Wright, M. E.; Cochran, B. B. J. Am. Chem. Soc. 1993, 115, 2059. (h) Zhou, J. Q.; Alper, H. Organometallics 1994, 13, 1586. (i) Monteil, F.; Matsuda, I.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4419.
20. For contributions from other laboratories, see: (a) Matsuda, I.; Ogiso, A.; Sato, S.; Izumi, Y. J. Am. Chem. Soc. 1989, 111, 2332. (b) Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120. (c) Matsuda, I.; Sakakibara, J.; Nagashima, H. Tetrahedron Lett. 1991, 32, 7431. (d) Matsuda, I.; Sakakibara, J.; Inoue, H.; Nagashima, H. Tetrahedron Lett. 1992, 33, 5799. (e) Doyle, M. P.; Shanklin, M. S. Organometallics 1993, 12, 11. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081. (g) Wright, M. E.; Cochran, B. B. J. Am. Chem. Soc. 1993, 115, 2059. (h) Zhou, J. Q.; Alper, H. Organometallics 1994, 13, 1586. (i) Monteil, F.; Matsuda, I.; Alper, H. J. Am. Chem. Soc. 1995, 117, 4419.
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28. The chemical shifts of 2-alkylbicyclo[3.3.0]octa-1,5-dien-3-one were reported to be 182-183 ppm (see ref 13). These data also confirm the β-silicon effect on the chemical shift of the C-1 carbon.
29. The values indicated by the Chem 3D program (MM2).
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32. Ojima, I.; Clos, N.; Donovan, R. J.; Ingallina, P. Organometallics 1991, 10, 3211.