Catalytic carbanion reactions: Formation and reaction of carbanions from ester or amide equivalents using catalytic amounts of bases

Chemistry - A European Journal

Volumn 15, Issue 41, 2009, Pages 10694-10700

  Kobayashi, Shu ^a   Matsubara, Ryosuke ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aldol reaction; Amides; Carbanions; Imines

Indexed keywords

ALDOL REACTION; CARBANIONS; CATALYTIC AMOUNTS; IMINES;

AMIDES; ESTERIFICATION; ESTERS;

IONS;

AMIDE; ANION; ESTER; IMINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

AMIDES; ANIONS; CATALYSIS; ESTERS; IMINES; MOLECULAR STRUCTURE;

EID: 70350214438     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901515     Document Type: Article

References (40)

1. a) H. O. House, Modern Synthetic Reactions, 2nd ed., Benjamin, New York, 1972, Chapter 9;
2. b) C. H. Heathcock in Comprehensive Organic Synthesis, Vol.2 (Ed.: B. M. Trost), Pergamon, Oxford, 1991, Chapter 1.5, pp. 133-180.
3. C. H. Heathcock in Comprehensive Organic Synthesis, Vol.2 (Ed. : B. M. Trost), Pergamon, Oxford, 1991, Chapter 1.6, pp. 181-238.
4. A.J. Waring in Comprehensive Organic Chemistry, Vol.1 (Ed.: J. F. Stoddart), Pergamon, Oxford, 1979, Chapter 5.2, pp. 1017-1104.
5. "Catalytic carbanion reaction" was first reported in the 8th International Symposium on Carbanion Chemistry (ISCC-8) at University of Wisconsin, Madison WI USA, 2007.
6. a) E. W. Colvin, Silicon Reagents in Organic Synthesis, Academic Press, New York, 1988, Chapter 15.1;
7. b) silyl enol ethers: S. Kobayashi, K. Manabe, H. Ishitani, J.-i. Matsuo, Sci. Synth. 2002, 4, 317;
8. c) C. Gennari, M. G. Beretta, A. Bernarde, G. Moro, C. Scolastico, R. Todeschini, Tetrahedron 1986, 42, 893.
9. For recent reviews of direct-type reactions, see: a) B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595 ;
10. b) B. List, Acc. Chem. Res. 2004, 37, 548;
11. c) W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580;
12. d) M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989;
13. e) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187;
14. f) A. Cardova, Acc. Chem. Res. 2004, 37, 102;
15. g)M. M. B. Marques, Angew. Chem. 2006, 118, 356;
16. Angew. Chem. Int. Ed. 2006, 45, 348;
17. h) M. Shibasaki, S. Matsunaga, J. Organomet. Chem. 2006, 691, 2089.
18. A few ester equivalents have been successfully employed in directtype reactions-acyl pyrrole: a) S. Harada, S. Handa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2005, 117, 4439;
19. Angew. Chem. Int. Ed. 2005, 44, 4365;
20. trichloromethyl ketone: b) H. Morimoto, S. H. Wiedemann, A. Yamaguchi, S. Harada, Z. Chen, S. Matsunaga, M. Shibasaki, Angew. Chem. 2006, 118, 3218;
21. Angew. Chem. Int. Ed. 2006, 45, 3146.
22. For example: D.A. Evans, S. G. Nelson, J. Am. Chem. Soc. 1997, 119, 6452.
23. For example: M. A. Stark, G. Jones, C. J. Richards, Organometallics 2000, 19,1282.
24. For examples: a) J. Christoffers, U. Rössler, T. Werner, Eur. J. Org. Chem. 2000, 701;
25. b) M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044;
26. c) M. Agostinho, S. Kobayashi, J. Am. Chem. Soc. 2008, 130, 2430.
27. For example: A. Singh, R. A. Yoder, B. Shen, J. N. Johnston, J. Am. Chem. Soc. 2007, 129, 3466.
28. For examples: a) S. Saito, T. Tsubogo, S. Kobayashi, J. Am. Chem. Soc. 2007, 129, 5364;
29. b) S. Kobayashi, T. Tsubogo, S. Saito, Y. Yamashita, Org. Lett. 2008, 10, 807;
30. c) S. Kobayashi, R. Yazaki, K. Seki, Y. Yamashita, Angew. Chem. 2008, 120, 5695;
31. Angew. Chem. Int. Ed. 2008, 47, 5613;
32. d) T. Tsubogo, S. Saito, K. Seki, Y. Yamashita, S. Kobayashi, J. Am,. Chem. Soc. 2008, 130, 13321.
33. S. Saito, S. Kobayashi, J. Am. Chem,. Soc. 2006, 128, 8704.
34. S. Saito, T. Tsubogo, S. Kobayashi, Chem. Commun. 2007, 1236.
35. a) R. Matsubara, F. Berthiol, S. Kobayashi, J. Am. Chem. Soc. 2008, 130, 1804;
36. b) R. Matsubara, S. Kobayashi, Synthesis 2008, 18, 3009;
37. c) S. B. J. Kan, R. Matsubara, F. Berthiol, S. Kobayashi, Chem. Commun. 2008, 6354;
38. d) V. H. Nguyen, R. Matsubara, S. Kobayashi, Angew. Chem. 2009, 121, 6041;
39. Angew. Chem. Int. Ed. 2009, 48, 5927;
40. e) R. Matsubara, F. Berthiol, V. H. Nguyen, S. Kobayashi, Bull. Chem. Soc. Jpn. 2009, 82,1083.