Catalytic Asymmetric Mannich-Type Reactions Using a Novel Chiral Iron Complex

Advanced Synthesis and Catalysis

Volumn 344, Issue 9, 2002, Pages 929-931

  Yamashita, Yasuhiro ^a   Ueno, Masaharu ^a   Kuriyama, Yokusu ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric catalysis; Iron; Lewis acid; Mannich reaction

Indexed keywords

EID: 0038340608     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200210)344:9<929::AID-ADSC929>3.0.CO;2-Z     Document Type: Article

References (36)

1. Reviews: a) H.-J. Knölker, A. Braier, D. J. Brocher, S. Cammerer, W. Frohner, P. Gonser, H. Hermann, D. Herzberg, K. R. Reddy, G. Rohde, Pure Appl. Chem. 2001, 73, 1075; b) W. A. Donaldson, Current Organic Chemistry 2000, 4, 837; c) H.-J. Knölker, Chem. Rev. 2000, 100, 2941; d) K. Ruck-Braun, M. Mikulas, P. Amrhein, Synthesis 1999, 727; e) T. Kauffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 386; f) B. Meunier, Chem. Rev. 1992, 92, 1411; g) D. Astruc, Chem. Met.-Carbon Bond 1987, 4, 625.
2. Reviews: a) H.-J. Knölker, A. Braier, D. J. Brocher, S. Cammerer, W. Frohner, P. Gonser, H. Hermann, D. Herzberg, K. R. Reddy, G. Rohde, Pure Appl. Chem. 2001, 73, 1075; b) W. A. Donaldson, Current Organic Chemistry 2000, 4, 837; c) H.-J. Knölker, Chem. Rev. 2000, 100, 2941; d) K. Ruck-Braun, M. Mikulas, P. Amrhein, Synthesis 1999, 727; e) T. Kauffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 386; f) B. Meunier, Chem. Rev. 1992, 92, 1411; g) D. Astruc, Chem. Met.-Carbon Bond 1987, 4, 625.
3. Reviews: a) H.-J. Knölker, A. Braier, D. J. Brocher, S. Cammerer, W. Frohner, P. Gonser, H. Hermann, D. Herzberg, K. R. Reddy, G. Rohde, Pure Appl. Chem. 2001, 73, 1075; b) W. A. Donaldson, Current Organic Chemistry 2000, 4, 837; c) H.-J. Knölker, Chem. Rev. 2000, 100, 2941; d) K. Ruck-Braun, M. Mikulas, P. Amrhein, Synthesis 1999, 727; e) T. Kauffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 386; f) B. Meunier, Chem. Rev. 1992, 92, 1411; g) D. Astruc, Chem. Met.-Carbon Bond 1987, 4, 625.
4. Reviews: a) H.-J. Knölker, A. Braier, D. J. Brocher, S. Cammerer, W. Frohner, P. Gonser, H. Hermann, D. Herzberg, K. R. Reddy, G. Rohde, Pure Appl. Chem. 2001, 73, 1075; b) W. A. Donaldson, Current Organic Chemistry 2000, 4, 837; c) H.-J. Knölker, Chem. Rev. 2000, 100, 2941; d) K. Ruck-Braun, M. Mikulas, P. Amrhein, Synthesis 1999, 727; e) T. Kauffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 386; f) B. Meunier, Chem. Rev. 1992, 92, 1411; g) D. Astruc, Chem. Met.-Carbon Bond 1987, 4, 625.
5. Reviews: a) H.-J. Knölker, A. Braier, D. J. Brocher, S. Cammerer, W. Frohner, P. Gonser, H. Hermann, D. Herzberg, K. R. Reddy, G. Rohde, Pure Appl. Chem. 2001, 73, 1075; b) W. A. Donaldson, Current Organic Chemistry 2000, 4, 837; c) H.-J. Knölker, Chem. Rev. 2000, 100, 2941; d) K. Ruck-Braun, M. Mikulas, P. Amrhein, Synthesis 1999, 727; e) T. Kauffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 386; f) B. Meunier, Chem. Rev. 1992, 92, 1411; g) D. Astruc, Chem. Met.-Carbon Bond 1987, 4, 625.
6. Reviews: a) H.-J. Knölker, A. Braier, D. J. Brocher, S. Cammerer, W. Frohner, P. Gonser, H. Hermann, D. Herzberg, K. R. Reddy, G. Rohde, Pure Appl. Chem. 2001, 73, 1075; b) W. A. Donaldson, Current Organic Chemistry 2000, 4, 837; c) H.-J. Knölker, Chem. Rev. 2000, 100, 2941; d) K. Ruck-Braun, M. Mikulas, P. Amrhein, Synthesis 1999, 727; e) T. Kauffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 386; f) B. Meunier, Chem. Rev. 1992, 92, 1411; g) D. Astruc, Chem. Met.-Carbon Bond 1987, 4, 625.
7. Reviews: a) H.-J. Knölker, A. Braier, D. J. Brocher, S. Cammerer, W. Frohner, P. Gonser, H. Hermann, D. Herzberg, K. R. Reddy, G. Rohde, Pure Appl. Chem. 2001, 73, 1075; b) W. A. Donaldson, Current Organic Chemistry 2000, 4, 837; c) H.-J. Knölker, Chem. Rev. 2000, 100, 2941; d) K. Ruck-Braun, M. Mikulas, P. Amrhein, Synthesis 1999, 727; e) T. Kauffmann, Angew. Chem. Int. Ed. Engl. 1996, 35, 386; f) B. Meunier, Chem. Rev. 1992, 92, 1411; g) D. Astruc, Chem. Met.-Carbon Bond 1987, 4, 625.
8. Reviews: a) J. P. Collman, Z. Wang, Chemtracts 1999, 12, 229; b) S. G. Davies, Aldrichimica Acta 1990, 23, 31.
9. Reviews: a) J. P. Collman, Z. Wang, Chemtracts 1999, 12, 229; b) S. G. Davies, Aldrichimica Acta 1990, 23, 31.
10. E. J. Corey, N. Imai, H.-Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728.
11. N. Khiar, I. Fernández, F. Alcudia, Tetrahedron Lett. 1993, 34, 123.
12. a) E. P. Kündig, B. Bourdin, G. Bernardinelli, Angew. Chem. Int. Ed. Engl. 1994, 33, 1856;
13. b) M. E. Bruin, E. P. Kündig, Chem. Commun. 1998, 2635;
14. c) E. P. Kündig, C. M. Saudan, F. Viton, Adv. Synth. Catal. 2001, 343, 51;
15. d) Quite recently, asymmetric 1,3-dipolar cycloaddition using a chiral Fe catalyst was reported, see: F. Viton, G. Bernardinelli, E. P. Kündig, J. Am. Chem. Soc. 2002, 124, 4968.
16. a) S. Kanemasa, Y. Oderaotoshi, H. Yamamoto, J. Tanaka, E. Wada, D. P. Curran, J. Org. Chem. 1997, 62, 6454;
17. b) S. Kanemasa, Y. Oderaotoshi, S. Sakaguchi, H. Yamamoto, J. Tanaka, E. Wada, J. Am. Chem. Soc. 1998, 120, 3074.
18. Whiting et al. have reported catalytic asymmetric aza-Diels-Alder reactions using a chiral iron-bisoxazoline complex, see: S. Bromidge, P. C. Wilson, A. Whiting, Tetrahedron Lett. 1998, 39, 8905.
19. Unpublished results; Hossain et al. have reported that a cyclopentadienyliron complex works as a Lewis acid to activate imines in the preparation of aziridines, see: a) M. F. Mayer, M. M. Hossain, J. Org. Chem. 1998, 63, 6839; b) M. Redlich, S. J. Mahmood, M. F. Mayer, M. M. Hossain, Synth. Commun. 2000, 30, 1401; c) M. F. Mayer, Q. Wang, M. M. Hossain, J. Organometallic Chem. 2001, 630, 78.
20. Unpublished results; Hossain et al. have reported that a cyclopentadienyliron complex works as a Lewis acid to activate imines in the preparation of aziridines, see: a) M. F. Mayer, M. M. Hossain, J. Org. Chem. 1998, 63, 6839; b) M. Redlich, S. J. Mahmood, M. F. Mayer, M. M. Hossain, Synth. Commun. 2000, 30, 1401; c) M. F. Mayer, Q. Wang, M. M. Hossain, J. Organometallic Chem. 2001, 630, 78.
21. Unpublished results; Hossain et al. have reported that a cyclopentadienyliron complex works as a Lewis acid to activate imines in the preparation of aziridines, see: a) M. F. Mayer, M. M. Hossain, J. Org. Chem. 1998, 63, 6839; b) M. Redlich, S. J. Mahmood, M. F. Mayer, M. M. Hossain, Synth. Commun. 2000, 30, 1401; c) M. F. Mayer, Q. Wang, M. M. Hossain, J. Organometallic Chem. 2001, 630, 78.
22. a) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 1997, 119, 7153;
23. b) S. Kobayashi, M. Ueno, H. Ishitani, J. Am. Chem. Soc. 1998, 120, 431;
24. c) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8180;
25. d) S. Kobayashi, Y. Hasegawa, H. Ishitani, Chem. Lett. 1998, 1131;
26. e) H. Ishitani, T. Kitazawa, S. Kobayashi, Tetrahedron Lett. 1999, 40, 2161;
27. f) S. Kobayashi, S. Komiyama, H. Ishitani, Angew. Chem. Int. Ed. Engl. 1998, 37, 979;
28. g) S. Kobayashi, K. Kusakabe, S. Komiyama, H. Ishitani, J. Org. Chem. 1999, 64, 4220;
29. h) S. Kobayashi, K. Kusakabe, H. Ishitani, Org. Lett. 2000, 2, 1225;
30. i) H. Ishitani, S. Komiyama, S. Kobayashi, Angew. Chem. Int. Ed. Engl. 1998, 37, 3186;
31. j) H. Ishitani, S. Komiyama, Y. Hasegawa, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 762;
32. k) T. Gastner, H. Ishitani, R. Akiyama, S. Kobayashi, Angew. Chem. Int. Ed. Engl. 2001, 40, 1896.
33. Wulff et al. also reported catalytic asymmetric Mannich-type reactions of imines prepared from o-aminophenol using a chiral Zr-VAPOL complex, see: S. Xue, S. Yu, Y. Deng, W. D. Wulff, Angew. Chem. Int. Ed. Engl. 2001, 40, 2271.
34. 2BINOL was an effective ligand in Zr-catalyzed asymmetric aldol reactions, see: a) H. Ishitani, Y. Yamashita, H. Shimizu, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 5403;
35. b) Y. Yamashita, H. Ishitani, H. Shimizu, S. Kobayashi, J. Am. Chem. Soc. 2002, 124, 3292.
36. In some metal-catalyzed asymmetric reactions, water affected the yields and selectivities, see: S. Ribe, P. Wipf, Chem. Commun. 2001, 299.