Asymmetric hydrogenation and allylic substitution reaction with novel chiral pinene-derived N,P-ligands

Tetrahedron Asymmetry

Volumn 20, Issue 12, 2009, Pages 1402-1406

  Meng, Xiangyan ^a   Li, Xinsheng ^a   Xu, Dongcheng ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IRIDIUM; PALLADIUM; PINENE; QUINOLINE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL ANALYSIS; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; PRODUCTIVITY; SUBSTITUTION REACTION;

EID: 67649649888     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.05.020     Document Type: Article

References (49)

1. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley, New York
2. Brown J.M. In: Jacobsen E.N., Pfaltz A., and Yamamoto H. (Eds). Comprehensive Asymmetric Catalysis Vol. I (1999), Springer, Berlin 121-182
3. For recent reviews on chiral P,N-ligands, see:. Helmchen G., and Pfaltz A. Acc. Chem. Res. 33 (2000) 336-345
4. Chelucci G., Orru G., and Pinna G.A. Tetrahedron 59 (2003) 9471-9515
5. Guiry P.J., and Saunders C.P. Adv. Synth. Catal. 346 (2004) 497-537
6. Zhou J., and Burgess K. Angew. Chem., Int. Ed. 46 (2007) 1129-1131
7. Cheruku P., Gohil S., and Andersson P.G. Org. Lett. 9 (2007) 1659-1661
8. Cheemala M.N., and Knochel P. Org. Lett. 9 (2007) 3089-3092
9. Wang A., Wüstenberg B., and Pfaltz A. Angew. Chem., Int. Ed. 47 (2008) 2298-2300
10. Lu S., and Bolm C. Angew. Chem., Int. Ed. 47 (2008) 8920-8923
11. Zhu Y., and Burgess K. Adv. Synth. Catal. 350 (2008) 979-983
12. Li S., Zhu S.-F., Zhang C.-M., Song S., and Zhou Q.-L. J. Am. Chem. Soc. 130 (2008) 8584-8585
13. Zhu Y., and Burgess K. J. Am. Chem. Soc. 130 (2008) 8894-8895
14. Cheruku P., Diesen J., and Andersson P.G. J. Am. Chem. Soc. 130 (2008) 5595-5599
15. Crabtree R.H., Felkin H., and Morris G.E. J. Organomet. Chem. 141 (1977) 205-215
16. Schnider P., Koch G., Prétôt R., Wang G., Bohnen F.M., Kruger C., and Pfaltz A. Chem. Eur. J. 3 (1997) 887-892
17. Lightfoot A., Schnider P., and Pfaltz A. Angew. Chem., Int. Ed. 37 (1998) 2897-2899
18. For review see:. Cui X., and Burgess K. Chem. Rev. 105 (2005) 3272-3296
19. Källström K., Munslow I.J., and Andersson P.G. Chem. Eur. J. 12 (2006) 3194-3200
20. Roseblade S.J., and Pfaltz A. C.R. Chim. 10 (2007) 178-187
21. Schrems M.G., Neumann E., and Pfaltz A. Angew. Chem., Int. Ed. 46 (2007) 8274-8276
22. Roseblade S.J., and Pfaltz A. Acc. Chem. Res. 40 (2007) 1402-1411
23. Wüstenberg B., and Pfaltz A. Adv. Synth. Catal. 350 (2008) 174-178
24. Kaukoranta P., Engman M., Hedberg C., Berquist J., and Andersson P.G. Adv. Synth. Catal. 350 (2008) 1168-1176
25. Schönleber M., Hilgraf R., and Pfaltz A. Adv. Synth. Catal. 350 (2008) 2033-2038
26. Diéguez M., Mazuela J., Pàmies O., Verendel J.J., and Andersson P.G. Chem. Commun. (2008) 3888-3890
27. Diéguez M., Mazuela J., Pàmies O., Verendel J.J., and Andersson P.G. J. Am. Chem. Soc. 130 (2008) 7208-7209
28. Engman M., Cheruku P., Tolstoy P., Bergquist J., Völker S.F., and Andersson P.G. Adv. Synth. Catal. 351 (2009) 375-378
29. Källström K., Hedberg C., Brandt P., Bayer A., and Andersson P.G. J. Am. Chem. Soc. 126 (2004) 14308-14309
30. Hedberg C., Källström K., Brandt P., Hansen L.K., and Andersson P.G. J. Am. Chem. Soc. 128 (2006) 2995-3001
31. Källström K., Munslow I.J., Hedberg C., and Andersson P.G. Adv. Synth. Catal. 348 (2006) 2575-2578
32. Engman M., Diesen J.S., Paptchikhine A., and Andersson P.G. J. Am. Chem. Soc. 129 (2007) 4536-4537
33. Cheruku P., Paptchikhine A., Ali M., Neudörfl J., and Andersson P.G. Org. Biomol. Chem. 6 (2008) 366-373
34. Bunlaksananusorn T., Polborn K., and Knochel P. Angew. Chem., Int. Ed. 42 (2003) 3941-3943
35. Kaiser S., Smidt S.P., and Pfaltz A. Angew. Chem., Int. Ed. 45 (2006) 5194-5197
36. Collomb P., and Zelewsky A.V. Tetrahedron: Asymmetry 6 (1995) 2903-2904
37. Collomb P., and Zelewsky A.V. Tetrahedron: Asymmetry 9 (1998) 3911-3917
38. Lötscher D., Rupprecht S., Stoeckli-Evans H., and Zelewsky A.V. Tetrahedron: Asymmetry 11 (2000) 4341-4357
39. Chelucci G., Gladiali S., Sanna M.G., and Brunner H. Tetrahedron: Asymmetry 11 (2000) 3419-3426
40. Chelucci G., and Cabras M.A. Tetrahedron: Asymmetry 7 (1996) 965-966
41. Malkov A.V., Bella M., Langer V., and Kočovsk P. Org. Lett. 2 (2000) 3047-3049
42. Malkov A.V., Baxendale I.R., Bella M., Langer V., Fawcett J., Russell D.R., Mansfield D.J., Valko M., and Kočovsky P. Organometallics 20 (2001) 673-690
43. Chelucci G., Saba A., and Soccolini F. Tetrahedron 57 (2001) 9989-9996
44. Verendel J.J., and Andersson P.G. Dalton Trans. (2007) 5603-5610
45. Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 724797). These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
46. Blankenstein J., and Pfaltz A. Angew. Chem., Int. Ed. 40 (2001) 4445-4447
47. Meng X., Li X., and Xu D. Chin. J. Org. Chem. 29 (2009) 629-633
48. Cheruku C., Gohil S., and Andersson P.G. Org. Lett. 9 (2007) 1659-1661
49. Xie J.-H., Duan H.-F., Fan B.-M., Cheng X., Wang L.-X., and Zhou Q.-L. Adv. Synth. Catal. 346 (2004) 625-632