Highly Enantioselective Hydrogenation of α-Dehydroamino Acids by Rhodium Complexes with New Unsymmetric P-Chirogenic Bisphosphine Ligands

Organic Letters

Volumn 3, Issue 3, 2001, Pages 373-375

  Ohashi, Atsushi ^a   Imamoto, Tsuneo ^a  

^a CHIBA UNIVERSITY   (Japan)

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ARTICLE;

EID: 0001099920     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006876s     Document Type: Article

References (23)

1. Reviews: (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; VCH publishers: Wheinheim, 2000. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994. (c) Hayashi, T.; Tomioka, K.; Yonemitsu, O. Asymmetric Synthesis; Kodansha: Tokyo, 1998. (d) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999. (e) Kagan, H. B. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, Chapter 1.
2. Reviews: (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; VCH publishers: Wheinheim, 2000. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994. (c) Hayashi, T.; Tomioka, K.; Yonemitsu, O. Asymmetric Synthesis; Kodansha: Tokyo, 1998. (d) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999. (e) Kagan, H. B. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, Chapter 1.
3. Reviews: (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; VCH publishers: Wheinheim, 2000. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994. (c) Hayashi, T.; Tomioka, K.; Yonemitsu, O. Asymmetric Synthesis; Kodansha: Tokyo, 1998. (d) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999. (e) Kagan, H. B. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, Chapter 1.
4. Reviews: (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; VCH publishers: Wheinheim, 2000. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994. (c) Hayashi, T.; Tomioka, K.; Yonemitsu, O. Asymmetric Synthesis; Kodansha: Tokyo, 1998. (d) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999. (e) Kagan, H. B. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, Chapter 1.
5. Reviews: (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; VCH publishers: Wheinheim, 2000. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994. (c) Hayashi, T.; Tomioka, K.; Yonemitsu, O. Asymmetric Synthesis; Kodansha: Tokyo, 1998. (d) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999. (e) Kagan, H. B. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1985; Vol. 5, Chapter 1.
6. Kagan, H. B.; Dang, T.-P. J. Am. Chem. Soc. 1972, 94, 6429.
7. Vineyard, B. D.; Knowles, W. S.; Sabacky, M. J.; Bachman, G. L.; Weinkauff, D. J. J. Am. Chem. Soc. 1977, 99, 5946.
8. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
9. (a) Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
10. (b) Burk, M. J. Angew. Chem., Int. Ed. 1998, 37, 1931.
11. Robin, F.; Mercier, F.; Richard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 3, 1365.
12. Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100.
13. (a) Yoshikawa, K.; Yamamoto, N.; Murata, M.; Awano, K.; Morimoto, T.; Achiwa, K. Tetrahedron: Asymmetry 1992, 3, 13.
14. (b) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
15. (c) Carmichael, D.; Doucet H.; Brown, J. M. Chem. Commun. 1999, 261.
16. Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
17. Ohashi, A.; Imamoto, T. Tetrahedron Lett., in press.
18. Nagata, K.; Matsukawa, S.; Imamoto, T. J. Org. Chem. 2000, 65, 4185.
19. (a) McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319.
20. (b) Mckinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145.
21. (a) Burk, M. J.; Gross, M. F.; Martinez, J. P. J. Am. Chem. Soc. 1995, 117, 9375.
22. (b) Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602.
23. 3, Z = 2, R = 0.055; Rw = 0.075; GOF = 1.75; bond lengths Rh1-P1 2.315(3) Å, Rh1-P2 2.316(3) Å, Rh1-nbd ca. 2.2 Å, bond angles P1-Rh1-P2 82.9(1)°, 1-Ad-P1-Me 106.3(6)°, t-Bu-P2-Me 104.8°, torsion angle P1-C-C-P2 48.2(9)°.