Rhodium-catalyzed asymmetric hydrogenation with aminophosphine ligands derived from 1,1′-binaphthyl-2,2′-diamine

Tetrahedron Letters

Volumn 43, Issue 38, 2002, Pages 6803-6806

  Guo, Rongwei ^a,b   Li, Xingshu ^a,b   Wu, Jing ^a,b   Kwok, Wai Him ^a,b   Chen, Jian ^a,b   Choi, Michael C K ^a,b   Chan, Albert S C ^a,b  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Amino acid derivatives; Aminophosphine ligand; Asymmetric hydrogenation; Rhodium

Indexed keywords

1,1 BINAPHTHYL 2,2' DIAMINE; ACRYLIC ACID DERIVATIVE; AMINE; AMINO ACID DERIVATIVE; AMINOPHOSPHINE; DIAMINE DERIVATIVE; LIGAND; NAPHTHYL GROUP; PHOSPHINE DERIVATIVE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; SYNTHESIS;

EID: 0037119710     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01510-1     Document Type: Article

References (39)

1. (c) Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; vols. I-III
2. Ojima I. Catalytic Asymmetric Synthesis. 2nd ed. 2000;John Wiley & Sons, New York, Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; vols. I-III.
3. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1993;John Wiley & Sons, New York.
4. Kagan H.B., Dang T.P. J. Chem. Soc. (D). 1971;481.
5. Vineyard B.D., Knowles W.S., Sabacky M.J., Bachman G.L., Weinkauff D.J. J. Am. Chem. Soc. 99:1977;5946-5952.
6. Miyashita A., Yasuda A., Takaya H., Toriumi K., Ito T., Souchi T., Noyori R. J. Am. Chem. Soc. 102:1980;7932-7934.
7. Noyori R., Ikeda T., Ohkuma T., Widhalm M., Kitamura M., Takaya H., Akutagawa S., Sayo N., Saito T., Taketomi T., Kumobayasji H. J. Am. Chem. Soc. 111:1989;9134-9135.
8. Togni A., Breutel C., Schnyder A., Spindler F., Landert H., Tijani A. J. Am. Chem. Soc. 116:1994;4062-4066.
9. Burk M.J. J. Am. Chem. Soc. 113:1991;8518-8519.
10. Burk M.J., Feaster J.E., Nugent W.A., Harlow R.L. J. Am. Chem. Soc. 115:1993;10125-10138.
11. Berens U., Burk M.J., Gerlach A., Hems W. Angew. Chem., Int. Ed. 39:2000;1981-1984.
12. Pai C.C., Lin C.W., Lin C.C., Chen C.C., Chan A.S.C. J. Am. Chem. Soc. 122:2000;11513-11514.
13. Yan Y.Y., RajanBabu T.V. Org. Lett. 2:2000;199-202.
14. Li W., Zhang X. J. Org. Chem. 65:2000;5871-5874.
15. Chan A.S.C., Hu W.H., Pai C.C., Lau C.P., Jiang Y.Y., Mi A.Q., Yan M., Sun J., Lou R.L., Deng J.G. J. Am. Chem. Soc. 119:1997;9570-9571.
16. RajanBabu T.V., Ayers T.A., Halliday G.A., You K.K., Calabrese J.C. J. Org. Chem. 62:1997;6012-6028.
17. Chen Y.X., Li X.S., Tong S.K., Choi M.C.K., Chan A.S.C. Tetrahedron Lett. 40:1999;957-960.
18. Selke R., Ohff M., Riepe A. Tetrahedron. 52:1996;15079-15102.
19. Reetz M.T., Neugebauer T. Angew. Chem., Int. Ed. 38:1999;179-181.
20. Reetz M.T., Mehler G. Angew. Chem., Int. Ed. 39:2000;3889-3891.
21. (b) Pastor, S. D.; Shum, S. P. Ciba Speciality Chemical Corperation US Patent 5,817,850, 1998
22. Reetz M.T., Gosberg A., Goddard R., Kyung S. Chem. Commun. 1998;2077-2078;
23. Reetz M.T., Sell T. Tetrahedron Lett. 41:2000;6333-6336.
24. van den Berg M., Minnaard A.J., Schudde E.P., van Esch J., de Vries A.H.M., de Vries J.G., Feringa B.L. J. Am. Chem. Soc. 122:2000;11539-11540.
25. Fiorini M., Giongo G.M. J. Mol. Catal. 7:1980;411-413.
26. Zhang F.Y., Pai C.C., Chan A.S.C. J. Am. Chem. Soc. 120:1998;5808-5809.
27. Schmid R., Broger E.A., Cereghetti M., Crameri Y., Foricher J., Lalonde M., Muller R.K., Scalone M., Schoettel G., Zutter U. Pure Appl. Chem. 68:1996;131-138.
28. Trabesinger G., Albinati A., Feiken N., Kunz R.W., Pregosin P.S., Tschoerner M. J. Am. Chem. Soc. 119:1997;6315-6323.
29. RajanBabu T.V., Ayers T.A., Casalnuovo A.L. J. Am. Chem. Soc. 116:1994;4101-4102.
30. RajanBabu T.V., Radetich B., You K.K., Ayers T.A., Casalnuovo A.L. J. Org. Chem. 64:1999;3429-3447.
31. Miyano S., Nawa M., Hashimoto H. Chem. Lett. 1980;729-730.
32. Miyano S., Nawa M., Mori A., Hashimoto H. Bull. Chem. Soc. Jpn. 1984;2171-2176.
33. Zhang F.Y., Kwok W.H., Chan A.S.C. Tetrahedron: Asymmetry. 12:2001;2337-2342.
34. 3): methyl carbons 21.09, 21.11.
35. 2): δ 0.21-0.27 (m, 2H), 0.56-0.61 (m, 2H), 0.73-1.60 (m, 40H), 3.77 (d, J=10.5 Hz, 2H), 6.84 (d, J=7.5 Hz, 2H), 7.03-7.10 (m, 4H), 7.67 (d, J=7.5 Hz, 2H), 7.73 (d, J=9.5 Hz, 2H), 7.78-7.81 (dd, J=4.5, 9.0 Hz, 2H).
36. 2. The enantiomeric excess and conversion were determined by GC. The hydrogenation product of acetamidoacrylic acid was converted to its methyl ester before the GC analysis with a capillary chiral column (CHROMPACK, CP Chirasil-DEX CB, 25 m×0.25 mm). Other hydrogenation products were analyzed using a (CHROMPACK, Chirasil-L-Val, 25 m×0.25 m) column.