Axially chiral electron-rich TunePhos-type ligand: synthesis and applications in asymmetric hydrogenation

Tetrahedron Letters

Volumn 50, Issue 42, 2009, Pages 5777-5779

  Zou, Yaping ^a   Geng, Huiling ^b   Zhang, Weicheng ^a   Yu, Shichao ^a   Zhang, Xumu ^a  

^a RUTGERS UNIVERSITY   (United States)

^b NORTHWEST A F UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA DEHYDROAMINO METHYL ESTER; DIMETHYL ITACONIC ACID; ESTER DERIVATIVE; ITACONIC ACID; LIGAND; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION;

EID: 69249240333     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.007     Document Type: Article

References (30)

1. Noyori R. Asymmetric Catalysis in Organic Synthesis (1994), Wiley, New York
2. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, Weinheim
3. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis I-III (1999), Springer, Berlin
4. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029
5. Shimizu H., Nagasaki I., and Saito T. Tetrahedron 61 (2005) 5405
6. Miyashita A., Yasuda A., Takaya H., Toriumi K., Ito T., Souchi T., and Noyori R. J. Am. Chem. Soc. 102 (1980) 7932
7. Noyori R. Angew. Chem., Int. Ed. 40 (2001) 40
8. Noyori R. Angew. Chem., Int. Ed. 41 (2002) 2008
9. Schmid R., Broger E.A., Cereghtti M., Crameri Y., Foricher J., Lalonde M., Muller R.K., Scalone M., Schoettel G., and Zutter U. Pure Appl. Chem. 68 (1996) 131
10. Saito T., Yokozawa T., Ishizaki T., Moroi T., Sayo N., Miura T., and Kumobayashi H. Adv. Synth. Catal. 343 (2001) 264
11. Pai C.C., Li Y.M., Zhou Z.Y., and Chan A.S.C. Tetrahedron Lett. 43 (2002) 2789
12. Paule S., Jeulin S., Ratovelomanana-Vidal V., Genêt J.P., Champion N., and Dellis P. Eur. J. Org. Chem. (2003) 1931
13. Jeulin S., Paule S., Ratovelomanana-Vidal V., Genet J.P., Champion N., and Dellis P. Angew. Chem., Int. Ed. 43 (2004) 320
14. Zhang Z., Qian H., Longmire J., and Zhang X. J. Org. Chem. 65 (2000) 6223
15. Wu S., Wang W., Tang W., Lin M., and Zhang X. Org. Lett. 4 (2002) 4495
16. Tang W., Wu S., and Zhang X. J. Am. Chem. Soc. 125 (2003) 9570
17. Lei A., Wu S., He M., and Zhang X. J. Am. Chem. Soc. 126 (2004) 1626
18. Wang C.-J., Sun X., and Zhang X. Angew. Chem., Int. Ed. 44 (2005) 4933
19. Wang C.-J., Sun X., and Zhang X. Synlett (2006) 1169
20. For a summary of the bite angle effect on enantioselectivity, see:. Zhang W., and Zhang X. Acc. Chem. Res. 40 (2007) 1278
21. Zhang, X. U.S. Patent 6,521,769, 2003 (filed 1999)
22. Sun X., Zhou L., Li W., and Zhang X. J. Org. Chem. 73 (2008) 1143
23. Li W., Sun X., Zhou L., Hou G., Yu S., and Zhang X. J. Org. Chem. 74 (2009) 1397
24. Wang C.-J., Wang C.-B., Chen D., Yang G., Wu Z., and Zhang X. Tetrahedron Lett. 50 (2009) 1038
25. Qiu L., Wu J., Chan S., Au-Yeung T.T.-L., Ji J.-X., Guo R., Pai C.-C., Zhou Z., Li X., Fan Q.-H., and Chan A.S.C. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5815
26. Qiu L., Kwong F.Y., Wu J., Lam W.H., Chan S., Yu W.-Y., Li Y.-M., Guo R., Zhou Z., and Chan A.S.C. J. Am. Chem. Soc. 128 (2006) 5955
27. Miyashita A., Karino H., Shimamura J.-I., Chiba T., Nagano K., Nohira H., and Takaya H. Chem. Lett. (1989) 1849
28. Shimizu H., Ishizaki T., Fujiwara T., and Saito T. Tetrahedron: Asymmetry 15 (2004) 2169
29. Initial attempt to employ the method used for the preparation of 7 (Ref. 9b) was found to be ineffective to synthesize the desired ligand 10.
30. 2: 647.4141, found: 647.4135.