Catalytic enone cycloallylation via concomitant activation of latent nucleophilic and electrophilic partners: Merging organic and transition metal catalysis

Journal of the American Chemical Society

Volumn 125, Issue 26, 2003, Pages 7758-7759

  Jellerichs, Bradley G ^a   Kong, Jong Rock ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONIC ACID; METAL; PALLADIUM;

ALLYLATION; ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; ENANTIOSELECTIVITY; ISOMERISM; REACTION OPTIMIZATION; REDUCTION;

ALKENES; ALLYL COMPOUNDS; CATALYSIS; CYCLIZATION; HYDROCARBONS, CYCLIC; KETONES; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES;

EID: 0038203414     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0301469     Document Type: Article

References (22)

1. For a review, see: Jang, H.-Y.; Cauble, D. F.; Huddleston, R. R.; Krische M. J. Acc. Chem. Res. 2003, 36, submitted.
2. For catalytic hydrometallative and carbometallative aldol and Michael cycloreductions, see: (a) Baik, T.-G.; Luis, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Jang, H.-Y.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143. (e) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
3. For catalytic hydrometallative and carbometallative aldol and Michael cycloreductions, see: (a) Baik, T.-G.; Luis, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Jang, H.-Y.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143. (e) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
4. For catalytic hydrometallative and carbometallative aldol and Michael cycloreductions, see: (a) Baik, T.-G.; Luis, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Jang, H.-Y.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143. (e) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
5. For catalytic hydrometallative and carbometallative aldol and Michael cycloreductions, see: (a) Baik, T.-G.; Luis, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Jang, H.-Y.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143. (e) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
6. For catalytic hydrometallative and carbometallative aldol and Michael cycloreductions, see: (a) Baik, T.-G.; Luis, A.-L.; Wang, L.-C.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 5112. (b) Wang, L.-C.; Jang, H.-Y.; Lynch, V.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 9448. (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 15156. (d) Huddleston, R. R.; Krische, M. J. Org. Lett. 2003, 5, 1143. (e) Cauble, D. F.; Gipson, J. D.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 1110.
7. For catalytic cycloadditions, see: (a) Baik, T.-G.; Wang, L.-C.; Luis, A.-L.; Krische, M. J. J. Am. Chem. Soc. 2001, 123, 6716.
8. (b) Wang, J.-C.; Ng, S.-S. Michael J. Krische J. Am. Chem. Soc. 2003, 125, 3682.
9. For catalytic cycloisomerizations, see: (a) Wang, L.-C.; Luis, A.-L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
10. (b) Agapiou, K.; Krische, M. J. Org. Lett 2003, 5, 1737.
11. For selected reviews, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
12. (b) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
13. For selected examples of two-component catalyst systems, see: (a) Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309. (b) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
14. For selected examples of two-component catalyst systems, see: (a) Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309. (b) Trost, B. M.; McEachern, E. J.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 12702.
15. For catalytic enone alkoxyallylation and hydroallylation, see: (a) Nakamura, H.; Sekido, M.; Ito, M.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 6838. (b) Muraoka, T.; Matsuda, I.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 9552.
16. For catalytic enone alkoxyallylation and hydroallylation, see: (a) Nakamura, H.; Sekido, M.; Ito, M.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 6838. (b) Muraoka, T.; Matsuda, I.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 9552.
17. Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
18. For a recent review, see: Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
19. For reviews, see: (a) Sarel, S. Acc. Chem. Res. 1978, 11, 204.
20. (b) Ohta, T.; Takaya, H. Metal Catalyzed Cycloaddition of Small Ring Compounds. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Eds.; Permagon: Oxford, 1991; Vol. 5, pp 1185-1205.
21. Keck, G. E.; Welch, D. S. Org. Lett. 2002, 4, 3687.
22. See, for example: Fukuyama, T.; Lin, S. C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050.