Efficient and practical Ag-catalyzed cycloadditions between arylimines and the Danishefsky diene

Journal of the American Chemical Society

Volumn 125, Issue 14, 2003, Pages 4018-4019

  Josephsohn, Nathan S ^a   Snapper, Marc L ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; IMINE; SILVER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALKENES; CATALYSIS; CYCLIZATION; IMINES; PIPERIDINES; SILVER; STEREOISOMERISM;

EID: 0037427326     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030033p     Document Type: Article

References (26)

1. Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15-23.
2. Kerwin, J. F.; Danishefsky, S. J. Tetrahedron Lett. 1982, 23, 3739-3742.
3. (a) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979-981. (b) Kobayashi, S.; Kusakabe, K.; Kimoyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 5220-5221. (c) Yao, S.; Johannsen, M.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 3121-3124. For a noncatalytic enantioselective cycloaddition, see: (d) Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264-3265.
4. (a) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979-981. (b) Kobayashi, S.; Kusakabe, K.; Kimoyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 5220-5221. (c) Yao, S.; Johannsen, M.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 3121-3124. For a noncatalytic enantioselective cycloaddition, see: (d) Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264-3265.
5. (a) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979-981. (b) Kobayashi, S.; Kusakabe, K.; Kimoyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 5220-5221. (c) Yao, S.; Johannsen, M.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 3121-3124. For a noncatalytic enantioselective cycloaddition, see: (d) Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264-3265.
6. (a) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979-981. (b) Kobayashi, S.; Kusakabe, K.; Kimoyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 5220-5221. (c) Yao, S.; Johannsen, M.; Hazell, R. G.; Jorgensen, K. A. Angew. Chem., Int. Ed. 1998, 37, 3121-3124. For a noncatalytic enantioselective cycloaddition, see: (d) Hattori, K.; Yamamoto, H. J. Org. Chem. 1992, 57, 3264-3265.
7. For previous reports regarding amino acid-based phosphine ligands, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523. (b) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (c) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (e) Degrado, S. J. Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (f) Hird, A. W.; Hoveyda, A. H. Agnew. Chem. Int. Ed. In press. (g) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. In press.
8. For previous reports regarding amino acid-based phosphine ligands, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523. (b) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (c) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (e) Degrado, S. J. Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (f) Hird, A. W.; Hoveyda, A. H. Agnew. Chem. Int. Ed. In press. (g) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. In press.
9. For previous reports regarding amino acid-based phosphine ligands, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523. (b) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (c) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (e) Degrado, S. J. Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (f) Hird, A. W.; Hoveyda, A. H. Agnew. Chem. Int. Ed. In press. (g) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. In press.
10. For previous reports regarding amino acid-based phosphine ligands, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523. (b) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (c) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (e) Degrado, S. J. Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (f) Hird, A. W.; Hoveyda, A. H. Agnew. Chem. Int. Ed. In press. (g) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. In press.
11. For previous reports regarding amino acid-based phosphine ligands, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523. (b) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (c) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (e) Degrado, S. J. Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (f) Hird, A. W.; Hoveyda, A. H. Agnew. Chem. Int. Ed. In press. (g) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. In press.
12. For previous reports regarding amino acid-based phosphine ligands, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523. (b) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (c) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (e) Degrado, S. J. Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (f) Hird, A. W.; Hoveyda, A. H. Agnew. Chem. Int. Ed. In press. (g) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. In press.
13. For previous reports regarding amino acid-based phosphine ligands, see: (a) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522-6523. (b) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (c) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (d) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. (e) Degrado, S. J. Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (f) Hird, A. W.; Hoveyda, A. H. Agnew. Chem. Int. Ed. In press. (g) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. In press.
14. (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668-1671.
15. (b) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704-1707.
16. (c) Hoveyda, A. H. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002; pp 991-1016.
17. (a) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285.
18. (b) Porter, J. R.; Wirschun, W. G.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 2657-2658.
19. (c) Jospehsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594-11599.
20. (d) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 984-985.
21. (e) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. L. J. Am. Chem. Soc. 2001, 123, 10409-10410.
22. See the Supporting Information for results of recycling studies.
23. Pelter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677-680.
24. For conjugate additions to the corresponding carbamates (cyclic products obtained), see: Comins, D. L.; LaMunyon, D. H.; Chen, X. J. Org. Chem. 1997, 62, 8182-8187.
25. Pilli, R. A.; Russowsky, D.; Dias, L. C. J. Chem. Soc., Perkin Trans. 1 1990, 1213-1214.
26. Bhattarai, K.; Cainelli, G.; Panunzio, M. Synlett. 1990, 229-230.