A catalyst for efficient and highly enantioselective hydrogenation of aromatic, heteroaromatic, and α,β-unsaturated ketones

Organic Letters

Volumn 2, Issue 26, 2000, Pages 4173-4175

  Burk, Mark J ^a   Hems, William ^a   Herzberg, Daniela ^a   Malan, Christophe ^a   Zanotti Gerosa, Antonio ^a  

^a Chirotech Technology Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001483542     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000309n     Document Type: Article

References (30)

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2. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
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6. Hydrosilylation: (a) Brunner, H.; Nishiyama, H.; Itoh, K. In Catalytic Asymmetric Synthesis: Ojima, I. Ed.; VCH: New York, 1993: Chapter 6.
7. (b) Sun, J.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5640.
8. Hydrogen transfer: (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97 and references therein.
9. (b) Jiang, Y.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1998, 120, 3817.
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12. (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675.
13. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.
14. (c) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872.
15. (a) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529.
16. (b) Ohkuma, T.; Koizumi, M.; Ikehira, H.; Yokozawa, T.; Noyori, R. Org. Lett. 2000, 2, 659.
17. (c) Ohkuma, T.; Koizumi, M.; Yoshida, M.; Noyori, R. Org. Lett. 2000, 2, 1749.
18. (a) Noyori, R.; Ohkuma, T. Pure Appl. Chem. 1999, 71, 1493.
19. (b) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T., Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495.
20. (c) Cao, P.; Zhang, X. J. Org. Chem. 1999, 64, 2127.
21. (d) Ikariya, T.; Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Seido, N.; Noyori, R. European Pat. Appl. EP 95308891. 1995.
22. For a recent example of a rhodium catalyst for enantioselective ketone hydrogenations, see: Jiang. Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100.
23. PhanePhos = 4,12-bis(diphenylphosphino)-[2.2]paracyclophane. (a) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
24. (b) Pye, P. J.; Rossen, K.; Reamer, R. A.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1998, 39, 4441.
25. DAIPEN = 1,1-dianisyl-2-isopropyl-1,2-ethylenediamine; see: Wey, S.-J.; O'Conner, K. J.; Burrows, C. J. Tetrahedron Lett. 1993, 34, 1905. DPEN = 1,2-diphenylethylenediamine. DACH = trans-1,2-diaminocyclohexane. AMP = 2-aminomethylpyrrolidine.
26. Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703
27. Xylyl-PhanePhos = 4,12-bis(di-3,5-xylylphosphino)-[2.2]paracy-clophane (xylyl refers to the 3.5-dimethylphenyl group). Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997.
28. Additional catalytic results are included in the Supplementary Information section.
29. Dyer, P. W.; Dyson, P. J.; James, S. L.; Martin, C. M.; Suman, P. Organometallics 1998, 17, 4344.
30. Strem Chemical Company provides research quantities of all three diamines. For comparison: DIAPEN ($12(X)/g). DPEN (SSO/g), DACH ($27/g).