Sc(OTf)3-catalyzed indolylation of 1,2-allenic ketones: Controlled highly selective synthesis of β-indolyl-α,β- unsaturetated (E)-enones and β,β-bisindolyl ketones

Organic Letters

Volumn 7, Issue 22, 2005, Pages 5063-5065

  Ma, Shengming ^a   Yu, Shichao ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; KETONE; MESYLIC ACID DERIVATIVE; ORGANOMETALLIC COMPOUND; SCANDIUM; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; INDOLES; KETONES; MESYLATES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SCANDIUM; STEREOISOMERISM;

EID: 27644599484     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052073z     Document Type: Article

References (37)

1. Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
2. (b) Sexton, J. E. Indoles (The Chemistry of Heterocyclic Compounds V. 25); Wiley: New York, 1983.
3. (c) Sundberg, R. J. Indoles; Academic Press: New York, 1996.
4. Kam, T. S. In Alkaloids, Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Amsterdam, 1999; Vol. 4.
5. (a) Irie, T.; Kubushirs, K.; Suzuki, K.; Tsukazaki, K.; Umezawa, K.; Nozawa, S. Anticancer Res. 1999, 31, 3061.
6. (b) Garbe, T. R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. J. Nat. Prod. 2000, 63, 596.
7. (c) Hong, C.; Firestone, G. L.; Bjeldanes, L. F. Biochem. Pharmacol. 2002, 63, 1085.
8. For some of the most recent papers, see: (a) Dyker, G..; Hildebrandt, D.; Liu, J. Merz, K. Angew. Chem., Int. Ed. 2003, 42, 4399.
9. (b) Yadav, J. S.; Reddy, B. V. S.; Padmavani, B.; Gupta, M. K. Tetrahedron Lett. 2004, 45, 7577 and references therein.
10. (c) Sharma, G. V. M.; Reddy, J. J.; Lakshmi, P. S.; Krishna, P. R. Tetrahedron Lett. 2004, 45, 7729.
11. (a) Szmuszkovicz, J. J. Am. Chem. Soc. 1957, 79, 2819.
12. (b) Iqbal, Z.; Jackson, A. H.; Rao, K. N. Tetrahedron Lett. 1988, 29, 2577.
13. (c) Dujardin, G.; Poirier, J. M. Bull. Soc. Chim. Fr. 1994, 131, 900.
14. (d) Harrington, P. E.; Kerr. M. A. Synlett 1996, 1047.
15. (e) Manabe, K.; Aoyama, N.; Kobayashi, S. Adv. Synth. Catal. 2001, 343, 174.
16. (f) Yadava, J. S.; Reddy, B. V. S.; Abraham, S.; Sabitha, G. Synthesis 2001, 2165.
17. (g) Bandini, M.; Cozzi, P. G.; Giacomini, M.; Melchiorre, P.; Selva, S.; Ronchi, A. U. J. Org. Chem. 2002, 67, 3700.
18. (h) Reddy, A. V.; Ravinder, K.; Goud, T. V.; Krishnaiah, P.; Raju, T. V.; Venkateswarlu, Y. Tetrahedron Lett. 2003, 44, 6257.
19. For some of the most recent reviews on the chemistry of allenes, see: (a) Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004; Vols. 1-2.
20. (b) Ma, S. Chem. Rev. 2005, 105, 2829.
21. (c) Ma, S. in Tsuji, J. Topics in Organometallic Chemistry-Palladium in Organic Synthesis; Springer-Verlag: Berlin, Heidelberg, 2005.
22. For some of the most recent typical reactions of allenes, see: (d) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438.
23. (e) Franzen, J.; Bäckvall, J.-E. J. Am. Chem. Soc. 2003, 125, 6056.
24. (f) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50.
25. (g) Chang, K.-J.; Rayabarapu, D. K.; Yang, F.-Y.; Cheng, C.-H. J. Am. Chem. Soc. 2005, 127, 126.
26. (h) Ng, S.-S.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 7320.
27. For recent reviews on the lanthanide complexes, see: (a) Mikami, K.; Terada, M.; Matsuzawa, H. Angew. Chem., Int. Ed. 2002, 41, 3554.
28. (b) Aspinall, H. C. Chem. Rev. 2002, 102, 1807.
29. (c) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187.
30. (d) Inanaga, J.; Furuno, H.; Hayano, T. Chem. Rev. 2002, 102, 2211.
31. Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673.
32. 3-catalyzed reactions in organic synthesis, see: (a) Kobayashi, S. Synlett 1994, 689.
33. (b) Kobayashi, S. Eur. J. Org. Chem. 1950, 15, 5.
34. Ibaceta-Lizana, Juana S. L.; Jackson, A. H.; Prasitpan, N.; Shannon, P. V. R. J. Chem. Soc., Perkin Trans. 2 1987, 1221.
35. For examples of the formation of α,β-unsaturated enones via the nucleophilic addition of 1,2-allenic ketones and the subsequent carbon-carbon double bond migration, see: (a) Gras, J. L.; Gallédow, B. S. Bull. Soc. Chim. Fr. 1983, II-89.
36. (b) Bertrand, M.; Gras, J. L. C. R. Acad. Sc. Paris 1965, 260, 6926.
37. (c) Cristau, H. J.; Viala, J.; Chritol, H. Tetrahedron Lett. 1982, 23, 1569.