C2-symmetric pyrrolidine-based chiral ammonium salts as a phase-transfer catalyst

Heterocycles

Volumn 83, Issue 11, 2011, Pages 2577-2588

  Ishikawa, Tatsuya ^a   Nagata, Kazuhiro ^a   Kani, Sachiko ^a   Matsuo, Mamoru ^a   Sano, Daisuke ^a   Kanemitsu, Takuya ^a   Miyazaki, Michiko ^a   Itoh, Takashi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80455131165     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-12254     Document Type: Article

References (20)

1. a) E. V. Dehmlow and S. S. Dehmlow, Phase Transfer Catalysis, 3rd ed.; VCH: Weinheim, 1993;
2. C. M. Stark, C. L. Liotta, and M. Halpern, Phase-Transfer Catalysis; Chapman and Hall: New York, 1994;
3. R. A. Jones, Quaternary Ammonium Salts: Their use in Phase Transfer Catalysis; Academic Press: San Diego, 2001.
4. U.-H. Dolling, P. Davis, and E. J. J. Grabowski, J. Am. Chem. Soc., 1984, 106, 446.
5. For reviews: a) T. Ooi and K. Maruoka, Angew. Chem. Int. Ed., 2007, 46, 4222;
6. M. J. O'Donnel, Acc. Chem. Res., 2004, 37, 506;
7. B. Lygo and B. I. Andrews, Acc. Chem. Res., 2004, 37, 518;
8. K. Maruoka and T. Ooi, Chem. Rev., 2003, 103, 3013.
9. a) K. Nagata, D. Sano, and T. Itoh, Synlett, 2007, 547;
10. D. Sano, K. Nagata, and T. Itoh, Org. Lett., 2008, 10, 1593;
11. K. Nagata, D. Sano, Y. Shimizu, M. Miyazaki, T. Kanemitsu, and T. Itoh, Tetrahedron: Asymmetry, 2009, 20, 2530.
12. Three reactions in which a chiral pyrrolidinium salt was used as a PTC were reported: a) B. Lygo, B. Allbutt, and S. R. James, Tetrahedron Lett., 2003, 44, 5629;
13. S. Arai, R. Tsuji, and A. Nishida, Tetrahedron Lett., 2002, 43, 9535;
14. M. Shi, K. Kazuta, Y. Satoh, and Y. Masaki, Chem. Pharm. Bull., 1994, 42, 2625.
15. Y. Yamamoto, J. Hoshino, Y. Fujimoto, J. Ohmoto, and S. Sawada, Synthesis, 1993, 298.
16. a) G. N. Grover, W. E. Kowtoniuk, and D. K. MacFarland, Tetrahedron Lett., 2006, 47, 57;
17. I. Cepanec, M. Litvic, H. Mikuldas, A. Bartolincic, and V. Vinkovic, Tetrahedron, 2003, 59, 2435.
18. N. Mase, T. Ohno, N. Hoshikawa, K. Ohishi, H. Morimoto, H. Yoda, and K. Takebe, Tetrahedron Lett., 2003, 44, 4073.
19. B. H. Kim, H. B. Lee, J. K. Hwang, and Y. G. Kim, Tetrahedron: Asymmetry, 2005, 16, 1215.
20. N-(Diphenylmethylene) glycine was produced as a side product, and no starting material was detected.