Organolanthanide-catalyzed cyclization/silylation of nitrogen-containing enynes

Journal of Organic Chemistry

Volumn 64, Issue 26, 1999, Pages 9697-9703

  Molander, Gary A ^a,b   Corrette, Christopher P ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACROMELIC ACID A; KAINIC ACID; LANTHANIDE; LUPININE; LUTETIUM; NITROGEN; PYRROLIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE; QUINOLIZIDINE DERIVATIVE; SILANE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

EID: 0033601347     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9913311     Document Type: Article

References (41)

1. (a) Molander, G. A. Chemtracts 1998, 11, 237, and references therein.
2. (b) Molander, G. A.; Dowdy, E. D.; Schumann, H. J. Org. Chem. 1998, 63, 3386.
3. (c) Molander, G. A.; Nichols, P. J.; Noll, B. C. J. Org. Chem. 1998, 63, 2292.
4. (d) Molander, G. A.; Nichols, P. J. J. Org. Chem. 1996, 61, 6040.
5. (e) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
6. (f) Onozawa, S.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1994, 35, 8177.
7. (g) Molander, G. A.; Dowdy, E. D. In Topics In Organometallic Chemistry. Kobayashi, S., Ed.; Springer-Verlag: New York, 1999; Vol. 2, pp 120-154.
8. (h) Fu, P.-F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157.
9. Molander, G. A.; Retsch, W. H. J. Am. Chem. Soc. 1997, 119, 8817.
10. Retsch, W. H. Ph.D. Thesis, University of Colorado at Boulder, 1997.
11. (a) Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
12. For other oxidation protocols, see: (b) Molander, G. A.; Corrette, C. P. Organometallics 1998, 17, 5504.
13. (c) Fleming, I.; Winter, S. B. D. Tetrahedron Lett. 1993, 34, 7287.
14. (d) Bergens, S. H.; Noheda, P.; Whelan, J.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 2121.
15. (e) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
16. Mattocks, A. R. Chemistry and Toxicology of Pyrrolizidine Alkaloids; Academic Press: New York, 1986; and references therein.
17. (a) Hua, D. H.; Miao, S. W.; Bravo, A. A.; Takemoto, D. J. Synthesis 1991, 970, and references therein.
18. (b) Veen, G.; Greinwald, R.; Witte, L.; Wray, V.; Czygan, F.-C. Phytochemistry 1991, 30, 1891.
19. Representative syntheses and isolations: (a) Ha, D.-C.; Ahn, J.-B.; Kwon, Y.-E. Bull. Kor. Chem. Soc. 1998, 19, 514. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574. (c) Kueger, H.; Benn, M. Heterocycles 1983, 20, 1331. (d) Ito, H.; Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 5469. (e) Pabreiter, C. M. Phytochemistry 1992, 31, 4135. (f) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (g) Yamada, K.; Tatematsu, H.; Unno, R.; Hirata, Y.; Hirono, I. J. Org. Chem. 1978, 29, 4543.
20. Representative syntheses and isolations: (a) Ha, D.-C.; Ahn, J.- B.; Kwon, Y.-E. Bull. Kor. Chem. Soc. 1998, 19, 514. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574. (c) Kueger, H.; Benn, M. Heterocycles 1983, 20, 1331. (d) Ito, H.; Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 5469. (e) Pabreiter, C. M. Phytochemistry 1992, 31, 4135. (f) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (g) Yamada, K.; Tatematsu, H.; Unno, R.; Hirata, Y.; Hirono, I. J. Org. Chem. 1978, 29, 4543.
21. Representative syntheses and isolations: (a) Ha, D.-C.; Ahn, J.- B.; Kwon, Y.-E. Bull. Kor. Chem. Soc. 1998, 19, 514. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574. (c) Kueger, H.; Benn, M. Heterocycles 1983, 20, 1331. (d) Ito, H.; Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 5469. (e) Pabreiter, C. M. Phytochemistry 1992, 31, 4135. (f) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (g) Yamada, K.; Tatematsu, H.; Unno, R.; Hirata, Y.; Hirono, I. J. Org. Chem. 1978, 29, 4543.
22. Representative syntheses and isolations: (a) Ha, D.-C.; Ahn, J.- B.; Kwon, Y.-E. Bull. Kor. Chem. Soc. 1998, 19, 514. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574. (c) Kueger, H.; Benn, M. Heterocycles 1983, 20, 1331. (d) Ito, H.; Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 5469. (e) Pabreiter, C. M. Phytochemistry 1992, 31, 4135. (f) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (g) Yamada, K.; Tatematsu, H.; Unno, R.; Hirata, Y.; Hirono, I. J. Org. Chem. 1978, 29, 4543.
23. Representative syntheses and isolations: (a) Ha, D.-C.; Ahn, J.- B.; Kwon, Y.-E. Bull. Kor. Chem. Soc. 1998, 19, 514. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574. (c) Kueger, H.; Benn, M. Heterocycles 1983, 20, 1331. (d) Ito, H.; Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 5469. (e) Pabreiter, C. M. Phytochemistry 1992, 31, 4135. (f) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (g) Yamada, K.; Tatematsu, H.; Unno, R.; Hirata, Y.; Hirono, I. J. Org. Chem. 1978, 29, 4543.
24. Representative syntheses and isolations: (a) Ha, D.-C.; Ahn, J.- B.; Kwon, Y.-E. Bull. Kor. Chem. Soc. 1998, 19, 514. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574. (c) Kueger, H.; Benn, M. Heterocycles 1983, 20, 1331. (d) Ito, H.; Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 5469. (e) Pabreiter, C. M. Phytochemistry 1992, 31, 4135. (f) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (g) Yamada, K.; Tatematsu, H.; Unno, R.; Hirata, Y.; Hirono, I. J. Org. Chem. 1978, 29, 4543.
25. Representative syntheses and isolations: (a) Ha, D.-C.; Ahn, J.- B.; Kwon, Y.-E. Bull. Kor. Chem. Soc. 1998, 19, 514. (b) Denmark, S. E.; Thorarensen, A.; Middleton, D. S. J. Org. Chem. 1995, 60, 3574. (c) Kueger, H.; Benn, M. Heterocycles 1983, 20, 1331. (d) Ito, H.; Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 5469. (e) Pabreiter, C. M. Phytochemistry 1992, 31, 4135. (f) Tatsuta, K.; Takahashi, H.; Amemiya, Y.; Kinoshita, M. J. Am. Chem. Soc. 1983, 105, 4096. (g) Yamada, K.; Tatematsu, H.; Unno, R.; Hirata, Y.; Hirono, I. J. Org. Chem. 1978, 29, 4543.
26. (a) Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun. 1999, 245.
27. (b) Chevliakov, M. V.; Montgomery, J. Angew. Chem., Int. Ed. Engl. 1998, 37, 3144.
28. Wang, K. K.; Brown, H. C. J. Am. Chem. Soc. 1982, 104, 7148.
29. Nichols, P. J. Ph.D. Thesis, University of Colorado at Boulder, 1997.
30. Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996.
31. The relative stereochemistry depicted for the bicyclic products was inferred from that determined by NOE difference spectroscopy for 16.
32. (a) Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275.
33. (b) Giardello, M. A.; Conticello, V. P.; Brard, L.; Gagné, M. R.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241.
34. (c) Arredondo, V. M.; Tian, S.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1999, 121, 3633.
35. Obora, Y.; Ohta, T.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1997, 119, 3745.
36. 3+ are 98 pm and 102 pm, respectively. Shannon, R. D. Acta Crystallogr. 1976, A32, 751.
37. The isolated product was found to be only 75% pure by GC analysis. See the Experimental Section.
38. The relative stereochemistry was determined by NOE difference spectroscopy.
39. Oxidation reactions with all of the azabicyclic products prepared in this study were attempted and failed to provide the desired alcohols upon purification. The problems associated with the oxidation of a similar system have been previously encountered. See ref 1d.
40. See, for example: Molander, G. A.; Dowdy, E. D.; Noll, B. C. Organometallics 1998, 17, 3754.
41. den Haan, K. H.; de Boer, J. L.; Teuben, J. H.; Smeets, W. J.; Spek, A. L. J. Organomet. Chem. 1987, 327, 31.