Catalytic asymmetric reaction of lithium ester enolates with imines

Chemical Communications

Volumn , Issue 8, 1999, Pages 715-716

  Tomioka, Kiyoshi ^a   Fujieda, Hiroki ^b   Hayashi, Satoko ^b   Hussein, Mostafa Ahmed ^a   Kambara, Takeshi ^a   Nomura, Yumiko ^c   Kanai, Motomu ^c   Koga, Kenji ^c  

^a KYOTO UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; ESTER; IMINE; LITHIUM;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; POLYMERIZATION;

EID: 0033591004     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901424a     Document Type: Article

References (19)

1. For reviews, see: D. J. Hart and D.-C. Ha, Chem. Rev., 1989, 89, 1447; E. F. Kleinman, in Comprehensive Organic Synthesis, ed. C. H. Heathcock, Pergamon, Oxford, 1991, vol. 2, ch. 4.1.
2. For reviews, see: D. J. Hart and D.-C. Ha, Chem. Rev., 1989, 89, 1447; E. F. Kleinman, in Comprehensive Organic Synthesis, ed. C. H. Heathcock, Pergamon, Oxford, 1991, vol. 2, ch. 4.1.
3. For representative examples, see: C. Baldoli and P. D. Buttero, J. Chem. Soc., Chem. Commun., 1991, 982; H. Fujioka, T. Yamanaka, N. Matsunaga, M. Fujii and Y. Kita, Synlett, 1992, 35; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; K. Hattori, M. Miyata and H. Yamamoto, J. Am. Chem. Soc., 1992, 115, 1151; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; M. Shimizu, Y. Teramoto and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729; R. N. Warrener, L. Liu and R. A. Russell, Chem. Commun., 1997, 2173.
4. For representative examples, see: C. Baldoli and P. D. Buttero, J. Chem. Soc., Chem. Commun., 1991, 982; H. Fujioka, T. Yamanaka, N. Matsunaga, M. Fujii and Y. Kita, Synlett, 1992, 35; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; K. Hattori, M. Miyata and H. Yamamoto, J. Am. Chem. Soc., 1992, 115, 1151; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; M. Shimizu, Y. Teramoto and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729; R. N. Warrener, L. Liu and R. A. Russell, Chem. Commun., 1997, 2173.
5. For representative examples, see: C. Baldoli and P. D. Buttero, J. Chem. Soc., Chem. Commun., 1991, 982; H. Fujioka, T. Yamanaka, N. Matsunaga, M. Fujii and Y. Kita, Synlett, 1992, 35; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; K. Hattori, M. Miyata and H. Yamamoto, J. Am. Chem. Soc., 1992, 115, 1151; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; M. Shimizu, Y. Teramoto and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729; R. N. Warrener, L. Liu and R. A. Russell, Chem. Commun., 1997, 2173.
6. For representative examples, see: C. Baldoli and P. D. Buttero, J. Chem. Soc., Chem. Commun., 1991, 982; H. Fujioka, T. Yamanaka, N. Matsunaga, M. Fujii and Y. Kita, Synlett, 1992, 35; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; K. Hattori, M. Miyata and H. Yamamoto, J. Am. Chem. Soc., 1992, 115, 1151; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; M. Shimizu, Y. Teramoto and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729; R. N. Warrener, L. Liu and R. A. Russell, Chem. Commun., 1997, 2173.
7. For representative examples, see: C. Baldoli and P. D. Buttero, J. Chem. Soc., Chem. Commun., 1991, 982; H. Fujioka, T. Yamanaka, N. Matsunaga, M. Fujii and Y. Kita, Synlett, 1992, 35; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; K. Hattori, M. Miyata and H. Yamamoto, J. Am. Chem. Soc., 1992, 115, 1151; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; M. Shimizu, Y. Teramoto and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729; R. N. Warrener, L. Liu and R. A. Russell, Chem. Commun., 1997, 2173.
8. For representative examples, see: C. Baldoli and P. D. Buttero, J. Chem. Soc., Chem. Commun., 1991, 982; H. Fujioka, T. Yamanaka, N. Matsunaga, M. Fujii and Y. Kita, Synlett, 1992, 35; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; K. Hattori, M. Miyata and H. Yamamoto, J. Am. Chem. Soc., 1992, 115, 1151; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; M. Shimizu, Y. Teramoto and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729; R. N. Warrener, L. Liu and R. A. Russell, Chem. Commun., 1997, 2173.
9. For representative examples, see: C. Baldoli and P. D. Buttero, J. Chem. Soc., Chem. Commun., 1991, 982; H. Fujioka, T. Yamanaka, N. Matsunaga, M. Fujii and Y. Kita, Synlett, 1992, 35; I. Ojima, Y. H. Park, C. M. Sun, T. Brigaud and M. Zhao, Tetrahedron Lett., 1992, 33, 5737; K. Hattori, M. Miyata and H. Yamamoto, J. Am. Chem. Soc., 1992, 115, 1151; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; M. Shimizu, Y. Teramoto and T. Fujisawa, Tetrahedron Lett., 1995, 36, 729; R. N. Warrener, L. Liu and R. A. Russell, Chem. Commun., 1997, 2173.
10. The recent situation with respect to the external ligand-controlled asymmetric reaction of organolithiums with imines has been summarized: S. E. Denmark and O. J.-C. Nicaise, Chem. Commun., 1996, 999; D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 1997, 8, 1895.
11. The recent situation with respect to the external ligand-controlled asymmetric reaction of organolithiums with imines has been summarized: S. E. Denmark and O. J.-C. Nicaise, Chem. Commun., 1996, 999; D. Enders and U. Reinhold, Tetrahedron: Asymmetry, 1997, 8, 1895.
12. Catalytic asymmetric addition of silyl enol ethers has been reported. H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 1997, 119, 7153; E. Hagiwara, A. Fujii and M. Sodeoka, J. Am. Chem. Soc., 1998, 120, 2474;
13. Catalytic asymmetric addition of silyl enol ethers has been reported. H. Ishitani, M. Ueno and S. Kobayashi, J. Am. Chem. Soc., 1997, 119, 7153; E. Hagiwara, A. Fujii and M. Sodeoka, J. Am. Chem. Soc., 1998, 120, 2474;
14. D. Ferraris, B. Young, T. Duddling and T. Lectka, J. Am. Chem. Soc., 1998, 120, 4548.
15. H. Fujieda, M. Kanai, T. Kambara, A. Iida and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; T. Kambara, M. A. Hussein, H. Fujieda, A. Iida and K. Tomioka, Tetrahedron Lett., 1998, 39, 9055.
16. H. Fujieda, M. Kanai, T. Kambara, A. Iida and K. Tomioka, J. Am. Chem. Soc., 1997, 119, 2060; T. Kambara, M. A. Hussein, H. Fujieda, A. Iida and K. Tomioka, Tetrahedron Lett., 1998, 39, 9055.
17. The absolute configuration and ee were determined according to the reported procedure (ref. 5).
18. However, 1,2-bis(dimethylamino)-1,2-diphenylethane was not a satisfactory ligand for the asymmetric conjugate addition reaction of organolithiums with unsaturated imines: M. Shindo, K. Koga and K. Tomioka, J. Org. Chem., 1998, 63, 9351.
19. K. Tomioka, M. Okuda, K. Nishimura, S. Manabe, M. Kanai, Y. Nagaoka and K. Koga, Tetrahedron Lett., 1998, 39, 2141.