A general synthesis of methylenecyclopentanes by a stereoselective [3 + 2] approach

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4959-4966

  Ghera, Eugene ^a   Yechezkel, Tamar ^a   Hassner, Alfred ^a  

^a BAR ILAN UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001662681     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960089k     Document Type: Article

References (36)

1. Synthetic Methods. 47. For part 46, see: Hassner, A.; Namboothiri, I. N. N. J. Organomet. Chem. In press.
2. For a review, see: Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467.
3. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
4. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
5. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
6. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
7. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
8. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
9. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
10. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
11. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
12. For [3 + 2] cyclopentanations (not included in ref 2), see, inter alia: Becker, D. A.; Danheiser, R. L. J. Am. Chem. Soc. 1989, 111, 389 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E.; Miller, R. F. J. Am. Chem. Soc. 1988, 110, 3300. Curran, D. P.; Chen, M. H. J. Am. Chem. Soc. 1987, 109, 6558. Herndon, J. W. J. Am. Chem. Soc. 1987, 109, 3165. Yamago, S.; Nakamura, E. J. Am. Chem. Soc. 1989, 111, 7285. Lee, T. V.; Richardson, K. A.; Ellis, K. L.; Visani, N. Tetrahedron 1989, 45, 1167. Panek, J. S.; Jarom, N. F. J. Org. Chem. 1993, 58, 2345. Knölker, H. J.; Graf, R. Synlett 1994, 131. Hudlicky, T.; Heard, N. E.; Fleming, A. J. Org. Chem. 1990, 55, 2570. Molander, G. A.; Schubert, D. C. J. Am. Chem. Soc. 1986, 108, 4683 and references therein.
13. Our results in this direction will be reported elsewhere.
14. For a review, see: Trost, B. M. Angew. Chem., Int. Ed. Engl. 1986, 25, 1.
15. Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5183. Breuilles, P.; Uguen, D. Tetrahedron Lett. 1988, 29, 201. Trost, B. M.; Mignani, S. M.; Nanninga, T. N. J. Am. Chem. Soc. 1988, 110, 1602. Trost, B. M.; Seoane, P.; Mignani, S.: Acemoglu, M. J. Am. Chem. Soc. 1989, 111, 7487.
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17. Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5183. Breuilles, P.; Uguen, D. Tetrahedron Lett. 1988, 29, 201. Trost, B. M.; Mignani, S. M.; Nanninga, T. N. J. Am. Chem. Soc. 1988, 110, 1602. Trost, B. M.; Seoane, P.; Mignani, S.: Acemoglu, M. J. Am. Chem. Soc. 1989, 111, 7487.
18. Shimizu, I.; Ohashi, Y.; Tsuji, J. Tetrahedron Lett. 1984, 25, 5183. Breuilles, P.; Uguen, D. Tetrahedron Lett. 1988, 29, 201. Trost, B. M.; Mignani, S. M.; Nanninga, T. N. J. Am. Chem. Soc. 1988, 110, 1602. Trost, B. M.; Seoane, P.; Mignani, S.: Acemoglu, M. J. Am. Chem. Soc. 1989, 111, 7487.
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23. Subsequent to our preliminary report (ref 10), a MIRC process involving the dilithiated chloro analog of 1 was reported to give stereomeric mixtures of methylcyclopentenes: Najera, C.; San Sano, J. Mo. Tetrahedron 1994, 50, 3491.
24. 2 and C=O). See: Oare, D. A.; Heathcock, C. H. In Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1989; Vol. 19, p 227. In an early report (ref 10) we made opposite designations for syn and anti. For monocyclic products (such as 15), the designations erythro and threo have been used in order to avoid misunderstandings.
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28. Hirama, M. Tetrahedron Lett. 1981, 22, 1905.
29. Steric obstruction between the cyclohexane ring and the phenylsulfonyl group probably prevent the cyclization of 15.
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31. Frazer-Reid, B.; Underwood, R.; Osterhout, M.; Grossman, J. A.; Liotta, D. L. J. Org. Chem. 1986, 51, 2152.
32. Ghera, E.; Yechezkel, T.; Hassner, A. J. Org. Chem. 1990, 55, 5977.
33. Trost, B. H.; Schrauff, N. S. J. Am. Chem. Soc. 1985, 107, 396.
34. Breuilles, P.; Uguen, D. Tetrahedron Lett. 1987, 28, 6053.
35. An excess of 1 was found necessary in order to prevent the formation of small amounts of a 1:2 donor/acceptor adduct originating from a Michael-Michael reaction.
36. The reactions of 8 with 9a were previously performed under different conditions; see ref 8 for configurational, spectroscopic, and analytical data of 10a and 11a.