A practical titanium-catalyzed synthesis of bicyclic cyclopentenones and allylic amines

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2713-2718

  Hicks, Frederick A ^a,c   Berk, Scott C ^b,c   Buchwald, Stephen L ^c  

^a NATIONAL SCIENCE FOUNDATION   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000146246     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951763l     Document Type: Article

References (43)

1. (a) For an extensive review, see: Negishi, E.-i. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1163-1184.
2. (b) Urabe, H.; Hata, T.; Sato, F. Tetrahedron Lett. 1995, 36, 4261.
3. Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1984, 106, 6422.
4. (a) Nugent, W. A.; Taber, D. F. J. Am. Chem Soc. 1989, 111, 6435
5. (b) Negishi, E.-i.; Swanson, D. R.; Lamaty, F.; Rousset, C. J. Tetrahedron Lett. 1989, 30, 5105.
6. Buchwald, S. L.; Grossman, R. B. J. Org. Chem 1992, 57, 5803.
7. Fagan, P. J.; Nugent, W. A.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 1880.
8. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 361.
9. (a) Berk, S. C.; Grossman, R B.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 4912.
10. (b) Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593.
11. Rasmussen, J. K.; Heilmann, S. M.; Krepski, L. R. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI Press: Greenwich, CT, 1991; pp 65-187.
12. For other examples of catalytic reactions involving group IV metallacycles, see: (a) Kabaloui, N. M.; Buchwald, S. L. J Am. Chem. Soc. 1995, 117, 6785. (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (c) Knight, K. S.; Waymouth, R. M. Tetrahedron Lett. 1992, 33, 7735 (d) Knight, K S.; Waymouth, R. M. Organometallics 1994, 13, 4542.
13. For other examples of catalytic reactions involving group IV metallacycles, see: (a) Kabaloui, N. M.; Buchwald, S. L. J Am. Chem. Soc. 1995, 117, 6785. (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (c) Knight, K. S.; Waymouth, R. M. Tetrahedron Lett. 1992, 33, 7735 (d) Knight, K S.; Waymouth, R. M. Organometallics 1994, 13, 4542.
14. For other examples of catalytic reactions involving group IV metallacycles, see: (a) Kabaloui, N. M.; Buchwald, S. L. J Am. Chem. Soc. 1995, 117, 6785. (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (c) Knight, K. S.; Waymouth, R. M. Tetrahedron Lett. 1992, 33, 7735 (d) Knight, K S.; Waymouth, R. M. Organometallics 1994, 13, 4542.
15. For other examples of catalytic reactions involving group IV metallacycles, see: (a) Kabaloui, N. M.; Buchwald, S. L. J Am. Chem. Soc. 1995, 117, 6785. (b) Crowe, W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787. (c) Knight, K. S.; Waymouth, R. M. Tetrahedron Lett. 1992, 33, 7735 (d) Knight, K S.; Waymouth, R. M. Organometallics 1994, 13, 4542.
16. Rausch, M. D.; Alt, H. G.; Kool, L. B.; Herberhold, M.; Thewalt, U.; Wolf, B. Angew. Chem., Int. Ed. Engl. 1985, 24, 394.
17. (a) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064.
18. (b) Jeony, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
19. (c) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286.
20. (d) Oppolzer, W. Pure Appl. Chem. 1990, 62, 1941.
21. (e) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656.
22. See ref 11c for a related iminocyclopentene.
23. Hart, D. J.; Kanai, K.-i.; Thomas, D. G.; Yang, T.-K. J. Org. Chem. 1983, 48, 289.
24. Hart D. J.; Ha, D.-C. Chem. Rev. 1989, 89, 1447.
25. Cainelli, G.; Panunzio, M.; Giacomini, D. Tetrahedron Lett. 1991, 32, 121.
26. Cainelli, G.; Mezzina, E ; Panunzio, M. Tetrahedron Lett. 1990, 31, 3481.
27. Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045.
28. For a review on the synthesis of allylic amines, see: Chaabouni, R.; Cheikh, R. D.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685. For a related synthesis of allylic amines with stoichiometric zirconium, see: Whitby, R. J.; Probert, G. D.; Coote, S. J. Tetrahedron Lett 1995, 36, 4113.
29. For a review on the synthesis of allylic amines, see: Chaabouni, R.; Cheikh, R. D.; Laurent, A.; Mison, P.; Nafti, A. Synthesis 1983, 685. For a related synthesis of allylic amines with stoichiometric zirconium, see: Whitby, R. J.; Probert, G. D.; Coote, S. J. Tetrahedron Lett 1995, 36, 4113.
30. For recent examples see: (a) Burgess, K.; Ohlmeyer. M. J. J. Org. Chem. 1991, 56, 1027. (b) Jung, M.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (c) Brunker, H.-G.; Adam, W. J. Am. Chem. Soc. 1995, 117, 3976.
31. For recent examples see: (a) Burgess, K.; Ohlmeyer. M. J. J. Org. Chem. 1991, 56, 1027. (b) Jung, M.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (c) Brunker, H.-G.; Adam, W. J. Am. Chem. Soc. 1995, 117, 3976.
32. For recent examples see: (a) Burgess, K.; Ohlmeyer. M. J. J. Org. Chem. 1991, 56, 1027. (b) Jung, M.; Rhee, H. J. Org. Chem. 1994, 59, 4719. (c) Brunker, H.-G.; Adam, W. J. Am. Chem. Soc. 1995, 117, 3976.
33. (a) Stutz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 320.
34. (b) Delaris, G.; Dunogues, J.; Gadras, A. Tetrahedron 1988, 44, 4293 and references therein.
35. For a review on hydride reductions of C=N, see: Hutchins, R. O.; Hutchins, M. K. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, pp 25-78.
36. Overman, L. E.; Okazaki, M. E.; Mishra, P. Tetrahedron Lett. 1986, 27, 4391.
37. Ojima, I.; Kogure, T.; Nagai, Y. Tetrahedron Lett. 1973, 2475.
38. The origins of the diastereoselectivites are unclear at the present time as the reduction of imines has received little mechanistic investigation.
39. The cyclization reaction itself results in two diastereomers at the TIPS ether carbon (Table 2. entries 7-9). For diastereoselectivities of entries 8 and 9, see ref 7b (also contains discussion on origins of selectivities). NMR experiments have shown the selectivity for entry 7 to be 2.2:1 in favor of the exo TIPS ether.
40. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.
41. Bartlett, A. J.; Laird, T ; Ollis, W. D. J. Chem. Soc., Perkin Trans. 1 1975, 1315.
42. Becu, C.; Anteunis, M. J. O. Bull. Soc. Chem. Belg 1987, 96, 115.
43. Corey, E. J.; Cho, H.; Rucker, C.; Hua, D. H. Tetrahedron Lett 1981, 22, 3455.