Asymmetric synthesis of bicyclic ketones having an angular substituent via Ti(II) alkoxide-mediated tandem cyclization of trisubstituted olefinic substrates

Organic Letters

Volumn 2, Issue 3, 2000, Pages 381-383

  Urabe, Hirokazu ^a   Hideura, Daigaku ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001726238     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9904038     Document Type: Article

References (45)

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2. For a review of the utility of five-membered bicyclic ketones, see: Trost, B. M. Chem. Soc. Rev. 1982, 11, 141-170. Paquette, L. A. In Topics in Current Chemistry; Boschke, F. L., Ed.; Springer-Verlag: Berlin, 1984; Vol. 119, pp 1-158. Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-719. Singh, V.; Thomas, B. Tetrahedron 1998, 54, 3647-3692.
3. For a review of the utility of five-membered bicyclic ketones, see: Trost, B. M. Chem. Soc. Rev. 1982, 11, 141-170. Paquette, L. A. In Topics in Current Chemistry; Boschke, F. L., Ed.; Springer-Verlag: Berlin, 1984; Vol. 119, pp 1-158. Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-719. Singh, V.; Thomas, B. Tetrahedron 1998, 54, 3647-3692.
4. For a review of the utility of five-membered bicyclic ketones, see: Trost, B. M. Chem. Soc. Rev. 1982, 11, 141-170. Paquette, L. A. In Topics in Current Chemistry; Boschke, F. L., Ed.; Springer-Verlag: Berlin, 1984; Vol. 119, pp 1-158. Mehta, G.; Srikrishna, A. Chem. Rev. 1997, 97, 671-719. Singh, V.; Thomas, B. Tetrahedron 1998, 54, 3647-3692.
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12. For the synthesis of (±)-isocomene and (±)-β-isocomene from (±)-1, see: Paquette, L. A.; Han, Y.-K. J. Am. Chem. Soc. 1981, 103, 1835-1838. Tobe, Y.; Yamashita, T.; Kakiuchi, K.; Odaira, Y. J. Chem. Soc., Chem. Commun. 1985, 898-899. For (±)-gymnomitrol and (±)-gymnomitrene from (±)-5, see: Welch, S. C.; Chayabunjonglerd, S. J. Am. Chem. Soc. 1979, 101, 6768-6769. Welch, S. C.; Chayabunjonglerd, S.; Rao, A. S. C. P. J. Org. Chem. 1980, 45, 4086-4093. See also: Dorsch, M.; Jäger, V.; Spönlein, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 798-799.
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22. For a review on the Group 4 metal-mediated cyclization and carbonylative cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
23. For a review on the Group 4 metal-mediated cyclization and carbonylative cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
24. For a review on the Group 4 metal-mediated cyclization and carbonylative cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
25. For a review on the Group 4 metal-mediated cyclization and carbonylative cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
26. For a review on the Group 4 metal-mediated cyclization and carbonylative cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
27. For a review on the Group 4 metal-mediated cyclization and carbonylative cyclization, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 1163-1184. Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696-1701. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Maier, M. In Organic Synthesis Highlights II; Waldmann, H., Ed.; VCH: Weinheim, 1995; pp 99-113. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
28. (a) Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5881-5898.
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36. The successful cases are so far limited to substrates having a nitrogen atom (coordination effect) or geminal substituents (Thorpe-Ingold effect) in their tether portion, which are not valid for 6. For a survey on the outcome of the cyclization of polysubstituted olefins with Group 4 metal reagents, see: ref 6. Negishi, E.; Maye, J. P.; Choueiry, D. Tetrahedron 1995, 51, 4447-4462. Yamaura, Y.; Mori, M. Tetrahedron Lett. 1999, 40, 3221-3224.
37. The successful cases are so far limited to substrates having a nitrogen atom (coordination effect) or geminal substituents (Thorpe-Ingold effect) in their tether portion, which are not valid for 6. For a survey on the outcome of the cyclization of polysubstituted olefins with Group 4 metal reagents, see: ref 6. Negishi, E.; Maye, J. P.; Choueiry, D. Tetrahedron 1995, 51, 4447-4462. Yamaura, Y.; Mori, M. Tetrahedron Lett. 1999, 40, 3221-3224.
38. See Supporting Information.
39. Whitesell, J. K. Chem. Rev. 1992, 92, 953-964. Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; p 513. Regan, A. C. J. Chem. Soc., Perkin Trans. 1 1999, 357-373.
40. Whitesell, J. K. Chem. Rev. 1992, 92, 953-964. Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; p 513. Regan, A. C. J. Chem. Soc., Perkin Trans. 1 1999, 357-373.
41. Whitesell, J. K. Chem. Rev. 1992, 92, 953-964. Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; p 513. Regan, A. C. J. Chem. Soc., Perkin Trans. 1 1999, 357-373.
42. Whitesell, J. K. Chem. Rev. 1992, 92, 953-964. Jones, G. B.; Chapman, B. J. Synthesis 1995, 475-497. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Wiley: New York, 1995; p 513. Regan, A. C. J. Chem. Soc., Perkin Trans. 1 1999, 357-373.
43. Although the clear explanation needs more experimental support, the different site selectivities of the protonation (to vinyl-Ti vs α-ester-Ti bonds) dependent upon the diastereomeric titanacycles 8 (eq 1) may account for this phenomenon.
44. Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericás, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389. Greene, A. E.; Charbonnier, F. Tetrahedron Lett. 1985, 26, 5525-5528.
45. Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericás, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388-9389. Greene, A. E.; Charbonnier, F. Tetrahedron Lett. 1985, 26, 5525-5528.