Asymmetric hydrogenation of itaconic acid and enol acetate derivatives with the Rh-TangPhos catalyst

Organic Letters

Volumn 5, Issue 2, 2003, Pages 205-207

  Tang, Wenjun ^a   Liu, Duan ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ITACONIC ACID; SUCCINIC ACID; RHODIUM; SUCCINIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; HYDROGENATION; ROOM TEMPERATURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETATES; CATALYSIS; HYDROGENATION; RHODIUM; STEREOISOMERISM; SUCCINATES; SUCCINIC ACIDS;

EID: 0038275889     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0272592     Document Type: Article

References (36)

1. Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.
2. For recent reviews of asymmetric hydrogenation, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 1. (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 121. (c) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 199. (d) Blaser, H.-U.; Spindler, F. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 247.
3. For recent reviews of asymmetric hydrogenation, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 1. (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 121. (c) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 199. (d) Blaser, H.-U.; Spindler, F. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 247.
4. For recent reviews of asymmetric hydrogenation, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 1. (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 121. (c) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 199. (d) Blaser, H.-U.; Spindler, F. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 247.
5. For recent reviews of asymmetric hydrogenation, see: (a) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis; Ojima. I., Ed.; Wiley-VCH: Weinheim, Germany, 2000; p 1. (b) Brown, J. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 121. (c) Ohkuma, T.; Noyori, R. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 199. (d) Blaser, H.-U.; Spindler, F. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalts, A., Yamamoto, H., Eds.; Springer: Berlin, Germany, 1999; p 247.
6. (a)Tang, W.; Zhang, X. Angew. Chem., Int. Ed. Engl. 2002, 41, 1612.
7. (b) Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159.
8. (a) Morimoto, T.; Chiba, M,; Achiwa, K. Tetrahedron Lett. 1990, 31, 261.
9. (b) Heitsch, H.; Henning, R.; Kleemann, H.-W.; Linz, W.; Nickel, W.-U.; Ruppert, D.; Urbach, H.; Wagner, A. J. Med. Chem. 1993, 36, 2788.
10. (a) Ojima, I.; Kogure, T.; Achiwa, K. Chem. Lett. 1978, 567. (b) Ojima, I.; Kogure, T. Chem. Lett. 1978, 1145.
11. (b) Ojima, I.; Kogure, T. Chem. Lett. 1978, 1145.
12. (c) Achiwa, K. Tetrahedron Lett. 1978, 1475.
13. (d) Christofel, W. C.; Vineyard, B. D. J. Am. Chem. Soc. 1979, 101, 4406.
14. (e) Kawano, H.; Ishii, Y.; Ikariya, T.; Saburi, M.; Yoshikawa, S.; Uchida, Y.; Kumamoto, N. Tetrahedron Lett. 1987, 28, 1905.
15. (f) Takahashi, H.; Achiwa, K. Chem. Lett. 1987, 1921.
16. (g) Takahashi, H.; Yamamoto, N.; Takeda, H.; Achiwa, K. Chem. Lett. 1989, 559.
17. (h) Inoguchi, K.; Morimoto, T.; Achiwa, K. J. Organomet. Chem. 1989, 370, C9.
18. (i) Chiba, T.; Miyashita, A.; Nohira, H.; Takaya Tetrahedron Lett. 1991, 32, 4745.
19. (j) Kuwano, R.; Sawamura, M.; Ito, Y. Tetrahedron: Asymmetry 1995, 6, 2521.
20. (k) Berens, U.; Burk, M. J.; Gerlach, A.; Hems, W. Angew. Chem., Int. Ed. 2000, 39, 1981.
21. (l) Gridnev, I.; Yamanoi, Y.; Higashi, N.; Tsuruta, H.; Yasutake, M.; Imamoto, T. Adv. Synth. Catal. 2001, 343, 118.
22. (a) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron lett. 1989, 30, 735.
23. (b) Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1993, 41, 1149.
24. (c) Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron 1993, 49, 1793.
25. (d) Jendralla, H.; Henning, R.; Seuring, B.; Herchen, J.; Kulitzscher, B.; Wunner, J. Synlett 1993, 155.
26. (e) Jendralla, H. Synthesis 1994, 494.
27. Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. 1998, 37, 1931.
28. Johnson, W. S.; Daub, G. H. Org. React. (N.Y.) 1951, 6, 1-73.
29. (a) Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
30. (b) Boaz, N. W. Tetrahedron Lett. 1998, 39, 5505.
31. (c) Burk, M. J.; Karlberg, C. S.; Pizzano, A. J. Am. Chem. Soc. 1998, 120, 4345.
32. (d) Jiang, Q.; Xiao, D.; Zhang, Z.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 516.
33. (e) Burk, M. J.; Stammers, T. A.; Straub, J. A. Org. Lett. 1999, 1, 387.
34. (f) Li, W.; Zhang, Z.; Xiao, D.; Zhang, X. J. Org. Chem. 2000, 65, 3489.
35. (a) Ohta, T.; Miyake, T.; Seido, N.; Kumobayashi, H.; Takaya, H. J. Org. Chem. 1995, 60, 357.
36. (b) Kuroki, Y.; Asada, D.; Sakamaki, Y.; Iseki, K. Tetrahedron Lett. 2000, 41, 4603.