Synthesis of tunable phosphinite-pyridine ligands and their applications in asymmetric hydrogenation

Tetrahedron Letters

Volumn 47, Issue 27, 2006, Pages 4733-4736

  Liu, Qi Bin ^a   Yu, Chang Bin ^a   Zhou, Yong Gui ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IRIDIUM; LIGAND; PHOSPHINE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CRYSTALLIZATION; ENANTIOSELECTIVITY; HYDROGENATION; LIGAND BINDING; SYNTHESIS;

EID: 33744534494     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.111     Document Type: Article

References (26)

1. Brown J.M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. 1 (1999), Springer, Berlin 121-182
2. Lightfoot A., Schnider P., and Pfaltz A. Angew. Chem., Int. Ed. 37 (1998) 2897-2899
3. Blankenstein J., and Pfaltz A. Angew. Chem., Int. Ed. 40 (2001) 4445-4447
4. Menges F., Neuburger M., and Pfaltz A. Org. Lett. 4 (2002) 4713-4716
5. Durry III W.J., Zimmerman N., Keenan M., Hayashi M., Kaiser S., Goddard R., and Pfaltz A. Angew. Chem., Int. Ed. 43 (2004) 70-74
6. Perry M.C., Cui X., Powell M., Hou D., Reibenspies J., and Burgess K. J. Am. Chem. Soc. 125 (2003) 113-123
7. Tang W., Wang W., and Zhang X. Angew. Chem., Int. Ed. 42 (2003) 943-946
8. Xu G., and Gilberston S.R. Tetrahedron Lett. 44 (2003) 953-955
9. Powell M.T., Hou D.-R., Perry M.C., Cui X., and Burgess K. J. Am. Chem. Soc. 123 (2001) 8878-8879
10. Bunlaksananurson T., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 42 (2003) 3941-3943
11. Schenkel L.B., and Ellman J.A. J. Org. Chem. 69 (2004) 1800-1802
12. Källström K., Hedberg C., Brandt P., Bayer A., and Andersson P.G. J. Am. Chem. Soc. 126 (2004) 14308-14309
13. Hedberg C., Källström K., Brandt P., Hansen L.K., and Andersson P.G. J. Am. Chem. Soc. 128 (2006) 2995-3001
14. For a recent review see:. Källström K., Munslow I., and Andersson P.G. Chem. Eur. J. 12 (2006) 3194-3200
15. and. Cui X., and Burgess K. Chem. Rev. 105 (2005) 3272-3296
16. Crabtree R.H. Acc. Chem. Res. 12 (1979) 331-338
17. During the course of preparing this manuscript, analogous N,P ligands applied in asymmetric hydrogenation of unfunctionalized, purely alkyl-substituted olefins have been independently developed by Pfaltz, the basic motif is slightly different (no methyl in 4-position of pyridine ring for Pfaltz's ligand), see:. Bell S., Wustenberg B., Kaiser S., Menges F., Netscher T., and Pfaltz A. Science 311 (2006) 642-644
18. Sakurai A., and Midorikawa A. Bull. Chem. Soc. Jpn. 41 (1968) 165-167
19. Lyle M.P.A., Narine A.A., and Wilson P.D. J. Org. Chem. 69 (2004) 5060-5064
20. Lyle M.P.A., Narine A.A., and Wilson P.D. Org. Lett. 6 (2004) 855-857
21. Rios R., Liang J., Lo M.M.-C., and Fu G.C. Chem. Commun. (2000) 377-378
22. The successful resolution of similar pyridine alcohols using optically active acids see:. Davies A.G., Kenyon J., and Thaker K. J. Chem. Soc. (1956) 3394
23. The diastereomeric resolution of very similar related compound see:. Kang J., Kim H.Y., and Kim J.H. Tetrahedron: Asymmetry 10 (1999) 2523-2533
24. For n = 0, the enantioselectivities at different temperature were as follows: 0 °C, 82% ee; 30 °C, 87% ee; 40 °C, 80% ee.
25. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551-5553
26. The absolute configuration of the product 7 was analogus to the configuration of most known compounds using (S)-Me-CBS asymmetric reduction.