Enantioselective synthesis of 3,3-disubstituted oxindoles through pd-catalyzed cyanoamidation

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3303-3306

  Yasui, Yoshizumi ^a   Kamisaki, Haruhi ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; INDOLE DERIVATIVE; NITRILE; OXINDOLE; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AMINATION; ANILINE COMPOUNDS; CATALYSIS; CYCLIZATION; INDOLES; NITRILES; PALLADIUM; STEREOISOMERISM;

EID: 49649118593     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801168j     Document Type: Article

References (41)

1. For a review, see: (a) Galliford, C. V.; Sheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748.
2. For recent examples, see: (b) Kolackowski, M.; Nowak, M.; Pawlowski, M.; Bojarski, A. J. J. Med. Chem. 2006, 49, 6732.
3. (c) Kato, H.; Yoshida, T.; Tokue, T.; Nojiri, Y.; Hirota, H.; Ohta, T.; Williams, R. M.; Tsukamoto, S. Angew. Chem., Int. Ed. 2007, 46, 2254.
4. (d) Uddin, M. K.; Reignier, S. G.; Coulter, T.; Montalbetti, C.; Grånäs, C.; Butcher, S.; Krog-Jensen, C.; Felding, J. Bioorg. Med. Chem. Lett. 2007, 17, 2854.
5. (e) Stevens, F. C.; Bloomquist, W. E.; Borel, A. G.; Cohen, M. L.; Droste, C. A.; Heiman, M. L.; Kriauciunas, A.; Shall, D. J.; Tinsley, F. C.; Jesudason, C. D. Bioorg. Med. Chem. Lett. 2007, 17, 6270.
6. (a) Dounay, A. B.; Hatanaka, K.; Kodanko, J. J.; Oestreich, M.; Overman, L. E.; Pfeifer, L. A.; Weiss, M. M J. Am. Chem. Soc. 2003, 125, 6261.
7. For recent studies, see: (b) McDermott, M. C.; Stephenson, G. R.; Walkington, A. J Synlett 2007, 51, and references cited therein.
8. Pinto, A.; Jia, Y.; Neuville, L.; Zhu, J. Chem. Eur. J. 2007, 13, 961.
9. Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402.
10. Kündig, E. P.; Seidel, T. M.; Jia, Y.-x.; Bernardinelli, G. Angew. Chem., Int. Ed. 2007, 46, 8484.
11. (a) Hills, I. D.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 3921.
12. (b) Shaw, S. A.; Aleman, P.; Vedejs, E. J. Am. Chem. Soc. 2003, 125, 13368.
13. Trost, B. M.; Zhang, Y. J. Am. Chem. Soc. 2006, 128, 4590.
14. Trost, B. M.; Cramer, N.; Bernsmann, H. J. Am. Chem. Soc. 2007, 129, 3086.
15. Lipase-catalyzed desymmetrization of 3,3-bis(hydroxymethyl)oxindole has also been reported; see: Akai, S.; Tsujino, T.; Akiyama, E.; Tanimoto, K.; Naka, T.; Kita, Y. J. Org. Chem. 2004, 69, 2478.
16. For addition of cyanoformamides to alkynes and alkenes, see: (a) Kobayashi, Y.; Kamisaki, H.; Yanada, R.; Takemoto, Y. Org. Lett. 2006, 8, 2711.
17. (b) Kobayashi, Y.; Kamisaki, H.; Takeda, H.; Yasui, Y.; Yanada, R.; Takemoto, Y. Tetrahedron 2007, 63, 2978.
18. For amide synthesis through coupling of chloroformamides and alkylboranes, see: Yasui, Y.; Tsuchida, S.; Miyabe, H.; Takemoto, Y. J. Org. Chem. 2007, 72, 5898.
19. For rhodium-catalyzed hydroamidation, see: Kobayashi, Y.; Kamisaki, H.; Yanada, K.; Yanada, R.; Takemoto, Y. Tetrahedron Lett. 2005, 46, 7549.
20. No report exists for transition-metal-catalyzed reaction of cyanoformamides except ref 10.
21. For general reactivity of cyanoformamides, see: (a) Oku, A.; Inoue, J.; Ueda, H.; Mashio, F Bull. Chem. Soc. Jpn. 1977, 50, 549, and references cited therein.
22. (b) Ford, R. E.; Knowles, P.; Lunt, E.; Marshall, S. M.; Penrose, A. J.; Ramsden, C. A.; Summers, A. J. H.; Walker, J. L.; Wright, D. E. J. Med. Chem. 1986, 29, 538.
23. Related transition-metal-catalyzed insertion reactions has been reported. Carbocyanation: (a) Nakao, Y.; Hirata, Y.; Tanaka, M.; Hiyama, T. Angew. Chem., Int. Ed. 2008, 47, 385, and references cited therein.
24. Cyanoesterification: (b) Nakao, Y.; Hirata, Y.; Hiyama, T. J. Am. Chem. Soc. 2006, 128, 7420.
25. (c) Nishihara, Y.; Inoue, Y.; Izawa, S.; Miyasaka, M.; Tanemura, K.; Nakajima, K.; Takagi, K Tetrahedron 2006, 62, 9872.
26. Bis(alkoxycarbonylation): (d) Liang, B.; Liu, J.; Gao, Y.-X.; Wongkhan, K.; Shu, D.-X.; Lan, Y.; Li, A.; Batsanov, A. S.; Howard, J. A. H.; Marder, T. B.; Chen, J.-H.; Yang, Z Organometallics 2007, 26, 4756, and references cited therein.
27. (e) Aratani, T.; Tahara, K.; Takeuchi, S.; Ukaji, Y.; Inomata, K. Chem. Lett. 2007, 36, 1328.
28. Cyanoformamides were synthesized from corresponding anilines. See the Supporting Information for details.
29. Hayashi, T. Acc. Chem. Res. 2000, 33, 354.
30. Morrison, J. D.; Burnett, R. E.; Agular, A. M.; Morrow, C. J.; Phillips, C. J. Am. Chem. Soc. 1971, 93, 1301.
31. For a review of using phosphonic acid and phosphinic acid derivatives as a ligand for transition metal-catalyzed reactions, see: Ansell, J.; Wills, M. Chem. Soc. Rev. 2002, 31, 259.
32. Tani, K.; Yamagata, T.; Nagata, K. Acta Crystallogr. 1994, C50, 1274.
33. Alexakis, A.; Mutti, S.; Normant, J. F. J. Am. Chem. Soc. 1991, 113, 6332.
34. Hulst, R.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 699.
35. de Vries, A. H. M.; Meetsma, A.; Feringa, B. L. Angew. Chem., Int. Ed. 1996, 35, 2374.
36. Badalassi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Arnold, A.; Feringa, B. L. Tetrahedron Lett. 1998, 39, 7795.
37. (a) Satoh, T.; Suzuki, S.; Suzuki, Y.; Miyaji, Y.; Imai, Z. Tetrahedron Lett. 1969, 4555.
38. (b) Heinzman, S. W.; Ganem, B. J. Am. Chem. Soc. 1982, 104, 6801.
39. Huang, A.; Kodanko, J. J.; Overman, L. E. J. Am. Chem. Soc. 2004, 126, 14043.
40. The corresponding pathway through cyanopalladation was excluded through previous studies; see ref 10b.
41. For similar discussion on enantioselective Heck reaction, see: Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.