Catalytic asymmetric cyclocarbonylation of nitrogen-containing enynes

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5547-5550

  Sturla, Shana J ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ENYNE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY;

EID: 0033597871     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990384f     Document Type: Article

References (33)

1. For a review of the Pauson-Khand reaction, see: (a) Geis, O.; Schmalz, H. G.; Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Ed.; Elsevier: New York, 1995; Vol. 12, p 703.
2. For a review of the Pauson-Khand reaction, see: (a) Geis, O.; Schmalz, H. G.; Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Ed.; Elsevier: New York, 1995; Vol. 12, p 703.
3. Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450.
4. For catalytic Pauson-Khand reactions see work cited in ref 2. Some subsequent advances in catalytic Pauson-Khand methodology include (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7637. (b) Belanger, D. B.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7641. (c) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (d) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
5. For catalytic Pauson-Khand reactions see work cited in ref 2. Some subsequent advances in catalytic Pauson-Khand methodology include (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7637. (b) Belanger, D. B.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7641. (c) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (d) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
6. For catalytic Pauson-Khand reactions see work cited in ref 2. Some subsequent advances in catalytic Pauson-Khand methodology include (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7637. (b) Belanger, D. B.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7641. (c) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (d) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
7. For catalytic Pauson-Khand reactions see work cited in ref 2. Some subsequent advances in catalytic Pauson-Khand methodology include (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7637. (b) Belanger, D. B.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7641. (c) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (d) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
8. For catalytic Pauson-Khand reactions see work cited in ref 2. Some subsequent advances in catalytic Pauson-Khand methodology include (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7637. (b) Belanger, D. B.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7641. (c) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (d) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
9. For catalytic Pauson-Khand reactions see work cited in ref 2. Some subsequent advances in catalytic Pauson-Khand methodology include (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7637. (b) Belanger, D. B.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7641. (c) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (d) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
10. For catalytic Pauson-Khand reactions see work cited in ref 2. Some subsequent advances in catalytic Pauson-Khand methodology include (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7637. (b) Belanger, D. B.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7641. (c) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (d) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
11. For catalytic Pauson-Khand reactions see work cited in ref 2. Some subsequent advances in catalytic Pauson-Khand methodology include (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7637. (b) Belanger, D. B.; Livinghouse T. Tetrahedron Lett. 1998, 39, 7641. (c) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782. (d) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142. (g) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (h) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
12. For a review of the asymmetric Pauson-Khand reaction, see Ingate S. T.; Marco-Contelles, J. Org. Prep. Proced. Int., 1998, 30, 121.
13. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688.
14. (a) Becker, D. P.; Flynn, D. L. Tetrahedron 1993, 49, 5047.
15. (b) Becker, D. P.; Flynn, D. L. Tetrahedron Lett. 1993, 34, 2087.
16. (c) Flynn, D. L.; Becker, D. P.; Spangler, D. P.; Nosai, R.; Gullikson, G. W.; Moummi, C.; Yang, D.-C. Bioorg. Med. Chem. Lett. 1992, 2, 1613.
17. (a) Yoo, S.-e.; Lee, S. H. J. Org. Chem. 1994, 59, 6968.
18. (b) Yoo, S.-E.; Lee, S.-H.; Jeong, N.; Cho, I. Tetrahedron Lett. 1993, 34, 3435.
19. (c) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1992, 169.
20. Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1992, 443.
21. 3C(O)N, HN, or LiN were subjected to the reaction conditions, an intractable mixture of products resulted.
22. X-ray structure parameters have been deposited in the Cambridge database.
23. We assume that all enones cyclized with the (S,S)-catalyst have the same absolute configuration.
24. The cyclization of (N-allyl-N-benzyl)-2-(1-hexynyl)aniline was carried out under the standard reaction conditions using 15% of the catalyst. The corresponding azabicyclo[4.3.0]nonenone was isolated in 70% yield, but with an ee of only 55%.
25. Masamune, S.; Choy, W.; Peterson, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
26. 3C(O)N) indicate this type of substrate to be incompatible with the catalyst system. We thank a referee for helpful comments on this issue.
27. Kocienski, P. J. Protecting Groups; Thieme: New York, 1994.
28. Chin, B.; Buchwald, S. L. J. Org. Chem. 1996, 61, 5650.
29. Xin, S.; Harrod, J. F. J. Organomet. Chem. 1995, 499, 181.
30. It is important to take appropriate safety precautions when using carbon monoxide, particularly at elevated pressure. All operations should be carried out in an efficient fume hood behind a blast shield.
31. Clive, D.; Cole, D.; Tao, Y. J. Org. Chem. 1994, 59, 1396.
32. Ward, D.; Rhee, C. Tetrahedron Lett. 1991, 32, 7165.
33. Berk, S. C.; Grossman, R. B.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8593.