Multicatalytic synthesis of α-pyrrolidinyl ketones via a tandem palladium(II)/indium(III)-catalyzed aminochlorocarbonylation/friedel-crafts acylation reaction

Journal of the American Chemical Society

Volumn 131, Issue 9, 2009, Pages 3124-3125

  Cernak, Tim A ^a   Lambert, Tristan H ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID CHLORIDES; ACYLATION REACTIONS; AROMATIC NUCLEOPHILES; CATALYTIC SEQUENCES; FRIEDEL-CRAFTS ACYLATION; OXIDATIVE CARBONYLATION;

ACIDS; ACYLATION; CARBONYLATION; CHLORINE COMPOUNDS; KETONES; PALLADIUM; PALLADIUM COMPOUNDS;

SYNTHESIS (CHEMICAL);

ALPHA PYRROLIDINYL KETONE; INDIUM 111; KETONE; PALLADIUM; UNCLASSIFIED DRUG; INDIUM; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBONYLATION; CHEMICAL REACTION; FRIEDEL CRAFTS REACTION; SYNTHESIS; ACYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ACYLATION; CATALYSIS; INDIUM; KETONES; MOLECULAR STRUCTURE; PALLADIUM; PYRROLIDINES; STEREOISOMERISM;

EID: 67749145466     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja809897f     Document Type: Article

References (32)

1. Tietze, L. F.; Brasche, G.; Gericke, K. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
2. For selected recent reviews on multicatalysis, see: (a) Ajamian, A.; Gleason, J. L. Angew. Chem., Int. Ed. 2004, 43, 3754.
3. (b) Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33, 302.
4. (c) Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
5. (d) Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
6. (e) Chapman, C. J.; Frost, C. G. Synthesis 2007, 1.
7. (f) Walji, A. M.; MacMillan, D. W. C. Synlett 2007, 1477.
8. Kelly, B. D.; Allen, J. M.; Tundel, R. E.; Lambert, T. H. Org. Lett. Submitted for publication.
9. (a) Semmelhack, M. F.; Zhask, A. J. Am. Chem. Soc. 1983, 105, 2034.
10. (b) Semmelhack, M. F.; Bodurow, C. J. Am. Chem. Soc. 1984, 106, 1496.
11. (c) Semmelhack, M. F.; Zhang, N. J. Org. Chem. 1989, 54, 4483.
12. (d) Semmelhack, M. F.; Kim, C.; Zhang, N.; Bodurow, C.; Sanner, M.; Dobler, W.; Meier, M. Pure Appl. Chem. 1990, 62, 2035.
13. (e) McCormick, M.; Monahan, M., III; Soria, J.; Goldsmith, D.; Liotta, D. J. Org. Chem. 1989, 54, 4485.
14. (f) White, J. D.; Hong, J.; Robarge, L. A. Tetrahedron Lett. 1999, 40, 1463.
15. (g) Holmes, C. P.; Bartlett, P. A. J. Org. Chem. 1989, 54, 98.
16. (a) Hegedus, L. S.; Allen, G. F.; Olsen, D. J. J. Am. Chem. Soc. 1980, 102, 3583.
17. (b) Hegedus, L. S.; McKearin, J. M. J. Am. Chem. Soc. 1982, 104, 2444.
18. (c) Hegedus, L. S.; Winton, P. M.; Varaprath, S. J. Org. Chem. 1981, 46, 2215.
19. (a) Beccalli, E. D.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
20. (b) Schmalz, H.-G.; Geis, O. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Vol. 2, p 2377.
21. A Beilstein substructure search indicated 1834 hits for natural products containing a pyrrolidinyl ring with β-oxygenation.
22. (a) Tsuji, J.; Morikawa, M.; Kiji, J. Tetrahedron Lett. 1963, 4, 1061.
23. (b) Bonnet, M. C.; Carmona, N.; Tkatchenko, I. J. Mol. Catal. A: Chem. 1999, 143, 181.
24. Heaney, H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 733.
25. 3 as an acylation catalyst, see: (a) Frost, C. G.; Hartley, J. P.; Griffin, D. Tetrahedron Lett. 2002, 43, 4789.
26. (b) Chapman, C. J.; Frost, C. G.; Hartley, J. P.; Whittle, A. J. Tetrahedron Lett. 2001, 42, 773.
27. (c) Chauhan, K. K.; Frost, C. G.; Love, I.; Waite, D. Synlett 1999, 1743. Also see ref 12d.
28. Support for this hypothesis was garnered by the observation of 2′, 4′-dimethoxypropiophenone and 2-(2, 4-dimethoxyphenyl)-N-tosylpyrrolidine in the crude reaction mixture.
29. (a) Yasuda, M.; Onishi, Y.; Ueba, M.; Miyai, T.; Baba, A. J. Org. Chem. 2001, 66, 7741.
30. (b) Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron Lett. 1998, 39, 6291.
31. (c) Miyai, T.; Onishi, Y.; Baba, A. Tetrahedron 1999, 55, 1017.
32. (d) Babu, S. A.; Yasuda, M.; Baba, A. Org. Lett. 2007, 9, 405.