One-Pot Sequential Asymmetric Hydrogenation Utilizing Rh(I) and Ru(II) Catalysts

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 428-429

  Doi, Takayuki ^a   Kokubo, Masaya ^a   Yamamoto, Keiji ^b   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002841863     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9720400     Document Type: Article

References (28)

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4. Omura, S.; Imamura, N.; Kawakita, K.; Mon, Y.; Yamazaki, Y.; Masuma, R.; Takahashi, Y.; Tanaka, H.; Huang, L.-Y.; Woodruff, H. J. Antibiot. 1986, 39, 1079. Katoh, I.; Yasunaga, T.; Ikawa, Y.; Yoshinaka, Y. Nature 1987, 329, 654.
5. For a review of the preparation of γ-amino β-hydroxy acids, see: Yokoyama, T.; Yuasa, Y.; Shibuya, S. Heterocycles 1992, 33, 1051.
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7. Dang, T. P.; Kagan, H. B. Chem. Commun. 1971, 481. Kagan, H. B.; Dang, T.-P. J. Am. Chem. Soc. 1972, 94, 6429. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc., Chem. Commun. 1972, 10.
8. Dang, T. P.; Kagan, H. B. Chem. Commun. 1971, 481. Kagan, H. B.; Dang, T.-P. J. Am. Chem. Soc. 1972, 94, 6429. Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc., Chem. Commun. 1972, 10.
9. Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856.
10. For reviews, see: Noyori, R. Asymmetric Catalysis In Organic Synthesis; John Wiley & Sons: Inc: New York, 1994. Koenig, K. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Inc.: New York, 1985; Vol. 5, p 71.
11. For reviews, see: Noyori, R. Asymmetric Catalysis In Organic Synthesis; John Wiley & Sons: Inc: New York, 1994. Koenig, K. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Inc.: New York, 1985; Vol. 5, p 71.
12. For the asymmetric hydrogenation of enamides, see: Kagan, H. B.; Langlois, N.; Dang, T. P. J. Organomet. Chem. 1975, 90, 353. Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894. Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. See also: Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M. Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
13. For the asymmetric hydrogenation of enamides, see: Kagan, H. B.; Langlois, N.; Dang, T. P. J. Organomet. Chem. 1975, 90, 353. Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894. Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. See also: Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M. Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
14. For the asymmetric hydrogenation of enamides, see: Kagan, H. B.; Langlois, N.; Dang, T. P. J. Organomet. Chem. 1975, 90, 353. Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894. Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. See also: Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M. Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
15. For the asymmetric hydrogenation of enamides, see: Kagan, H. B.; Langlois, N.; Dang, T. P. J. Organomet. Chem. 1975, 90, 353. Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894. Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. See also: Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M. Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
16. For the asymmetric hydrogenation of enamides, see: Kagan, H. B.; Langlois, N.; Dang, T. P. J. Organomet. Chem. 1975, 90, 353. Morimoto, T.; Chiba, M.; Achiwa, K. Chem. Pharm. Bull. 1992, 40, 2894. Burk, M. J.; Wang, Y. M.; Lee, J. R. J. Am. Chem. Soc. 1996, 118, 5142. See also: Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M. Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117. Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 5985.
17. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
18. Sinou, D.; Kagan, H. B. J. Organomet. Chem. 1976, 114, 325.
19. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
20. Burk, M. J.; Feaster, J. E.; Nugent, W. A.; Harlow, R. L. J. Am. Chem. Soc. 1993, 115, 10125. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
21. In the absence of triethylamine, no reaction occurred under 10 atm of hydrogen. Improvement of enantioselectivity by the addition of triethylamine in the Rh(I)-catalyzed asymmetric hydrogenation of α-acetamino-cinnamic acid has been reported; see ref 5.
22. Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Caño De Andrade, M. C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 665.
23. Nishi, T.; Kitamura, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett. 1988, 29, 6327.
24. 2 90 atm, 60°C, 24 h) resulted in a 62:38 mixture of 2a and 3a, with enantiomeric excesses of 88% and 83% ee, respectively.
25. No reduction of la by the Ru(II)-catalyst under 10 atm of hydrogen was observed at 40°C, although the asymmetric hydrogenation of β-keto esters using the same catalyst has been reported. See: Genêt, J. P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Caño De Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte, J. A. Tetrahedron: Asymmetry 1994, 5, 675.
26. One of the reviewers suggested that the addition of triethylamine might slightly inhibit the Ru(II)-BINAP-catalyzed hydrogenation of β-keto esters; see: King, S. A.; Thompson, A. S.; King, A. O.; Verhoeven, T. R. J. Org. Chem. 1992, 57, 6689. We thank the reviewer for this suggestion.
27. 2[(S)-BINAP] as catalysts gave a 1:1 mixture of racemic 2a and 3a.
28. Chiral induction for 4S and 4R was calculated on the basis of the experimental results of the one-pot reaction: 76:24 (52% ee).