Asymmetric hydrogenation of α,β-unsaturated carboxylic acids in supercritical carbon dioxide

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2813-2816

  Xiao, Jianliang ^a   Nefkens, Sylvia C A ^a   Jessop, Philip G ^a   Ikariya, Takao ^a   Noyori, Ryoji ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLBUTYRIC ACID;

ARTICLE; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029995329     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00436-4     Document Type: Article

References (23)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. Subramaniam, B.; McHugh, M. A. Ind. Eng. Chem. Process Des. Dev. 1986, 25, 1.
3. Brennecke, J. F. In Supercritical Fluid Engineering Science: Fundamentals and Applications; Kiran, E., Brennecke, J. F., Eds.; ACS Symposium Series 514; American Chemical Society: Washington, DC, 1993; p 201.
4. Kaupp, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1452.
5. Jessop, P. G.; Ikariya, T.; Noyori, R. Science 1995, 269, 1065.
6. 2: Burk, M. J.; Feng, S.; Gross, M. F.; Tumas, W. J. Am. Chem. Soc. 1995, 117, 8277.
7. Zhang, X.; Uemura, T.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Takaya, H. Synlett 1994, 501.
8. 1H NMR analysis of the carboxylic acid using (R)-α-naphthylethylamine as a chiral shift reagent according to a method modified from reference 10.
9. Ohta, T.; Takaya, H.; Kitamura, M.; Nagai, K.; Noyori, R. J. Org. Chem. 1987, 52, 3174.
10. Ashby, M. T.; Halpern, J. J. Am. Chem. Soc. 1991, 113, 589.
11. Ohta, T.; Takaya, H.; Noyori, R. Inorg. Chem. 1988, 27, 566.
12. Jessop, P. G.; Ikariya, T.; Noyori, R. Nature 1994, 368, 231.
13. Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 8851.
14. Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori, R. J. Chem. Soc., Chem. Commun. 1995, 707.
15. Jessop, P. G.; Ikariya, T.; Noyori, R. Chem. Rev. 1995, 95, 259.
16. Ting, S. S. T.; Macnaughton, S. J.; Tomasko, D. L.; Foster, N. R. Ind. Eng. Chem. Res. 1993, 32, 1471; Dobbs, J. M.; Wong, J. M.; Lahiere, R. J.; Johnston, K. P. Ind. Eng. Chem. Res. 1987, 26, 56.
17. Ting, S. S. T.; Macnaughton, S. J.; Tomasko, D. L.; Foster, N. R. Ind. Eng. Chem. Res. 1993, 32, 1471; Dobbs, J. M.; Wong, J. M.; Lahiere, R. J.; Johnston, K. P. Ind. Eng. Chem. Res. 1987, 26, 56.
18. Phase tests using a sapphire window-equipped reactor showed that the reactions with or without additives took place in a single homogeneous phase under the conditions used.
19. Ohta, T.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1990, 31, 7189.
20. 3). The deuterium content, as determined by NMR analysis, was C(2) position 0.97, C(3) position 0.97, and carboxylic acid proton position 0.76. This result confirmed D2/carboxylic acid isotope exchange. The lower value at the carboxylic acid proton position could be caused by adventitious water during workup.
21. Linn, D. E., Jr.; Halpern, J. J. Am. Chem. Soc. 1987, 109, 2969.
22. Kirss, R. U.; Eisenschmid, T. C.; Eisenberg, R. J. Am. Chem. Soc. 1988, 110, 8564.
23. Jessop, P. G.; Morris, R. H. Coord. Chem. Rev. 1992, 121, 155.