Remote ester group leads to efficient kinetic resolution of racemic aliphatic alcohols via asymmetric hydrogenation

Journal of the American Chemical Society

Volumn 136, Issue 50, 2014, Pages 17426-17429

  Yang, Xiao Hui ^a   Wang, Ke ^a   Zhu, Shou Fei ^a   Xie, Jian Hua ^a   Zhou, Qi Lin ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; ESTERS; HYDROGENATION; IRIDIUM COMPOUNDS;

ALIPHATIC ALCOHOL; ASYMMETRIC HYDROGENATION; CATALYST LOADINGS; HIGH ENANTIOSELECTIVITY; HYDROXY ESTERS; HYDROXYL GROUPS; IRIDIUM COMPLEX; KINETIC RESOLUTION;

LOADING;

ALKANOL; DELTA ALKYL 1,5 DIOL; DELTA ALKYL DELTA HYDROXY ESTER; ESTER; HYDROXYL GROUP; IRIDIUM COMPLEX; UNCLASSIFIED DRUG; ALCOHOL DERIVATIVE; COORDINATION COMPOUND; IRIDIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; RACEMIC MIXTURE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM;

ALCOHOLS; CATALYSIS; COORDINATION COMPLEXES; ESTERS; HYDROGENATION; IRIDIUM; KINETICS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84919384159     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja510990v     Document Type: Article

References (55)

1. Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40
2. Reetz, M. T.; Li, X. J. Am. Chem. Soc. 2006, 128, 1044
3. Li, J.; Tang, Y.; Wang, Q.; Li, X.; Cun, L.; Zhang, X.; Zhu, J.; Li, L.; Deng, J. J. Am. Chem. Soc. 2012, 134, 18522
4. de Vries, J. G.; Elsevier, C. J. The Handbook of Homogeneous Hydrogenation; Wiley-VCH: Weinheim, Germany, 2007.
5. Zhao, B.; Han, Z.; Ding, K. Angew. Chem., Int. Ed. 2013, 52, 4744
6. Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sin. 2012, 70, 1427
7. Jiang, Q.; Jiang, Y.; Xiao, D.; Cao, P.; Zhang, X. Angew. Chem., Int. Ed. 1998, 37, 1100
8. Ohkuma, T.; Sandoval, C. A.; Srinivasan, R.; Lin, Q.; Wei, Y.; Muñiz, K.; Noyori, R. J. Am. Chem. Soc. 2005, 127, 8288
9. Yamamura, T.; Nakatsuka, H.; Tanaka, S.; Kitamura, M. Angew. Chem., Int. Ed. 2013, 52, 9313
10. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974
11. Denmark, S. E.; Beutner, G. L. Angew. Chem., Int. Ed. 2008, 47, 1560
12. Müller, C. E.; Schreiner, P. R. Angew. Chem., Int. Ed. 2011, 50, 6012
13. Pellissier, H. Adv. Synth. Catal. 2011, 353, 1613
14. Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1996, 118, 1809
15. Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492
16. Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091
17. Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638
18. Vasbinder, M. M.; Jarvo, E. R.; Miller, S. J. Angew. Chem., Int. Ed. 2001, 40, 2824
19. Mizuta, S.; Sadamori, M.; Fujimoto, T.; Yamamoto, I. Angew. Chem., Int. Ed. 2003, 42, 3383
20. Birman, V. B.; Uffman, E. W.; Jiang, H.; Li, X.; Kilbane, C. J. J. Am. Chem. Soc. 2004, 126, 12226
21. Matsumura, Y.; Maki, T.; Murakami, S.; Onomura, O. J. Am. Chem. Soc. 2003, 125, 2052
22. Spivey, A. C.; Leese, D. P.; Zhu, F.; Davey, S. G.; Jarvest, R. L. Tetrahedron 2004, 60, 4513
23. Gissibl, A.; Finn, M. G.; Reiser, O. Org. Lett. 2005, 7, 2325
24. Mazet, C.; Roseblade, S.; Köhler, V.; Pfaltz, A. Org. Lett. 2006, 8, 1879
25. Hu, B.; Meng, M.; Wang, Z.; Du, W.-T.; Fossey, J. S.; Hu, X.-Q.; Deng, W.-P. J. Am. Chem. Soc. 2010, 132, 17041
26. Hashiguchi, S.; Fujii, A.; Haack, K.-J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288
27. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725
28. Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475
29. Sun, W.; Wang, H.; Xia, C. G.; Li, J.; Zhao, P. Angew. Chem., Int. Ed. 2003, 42, 1042
30. Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835
31. Mandal, S. K.; Sigman, M. S. J. Org. Chem. 2003, 68, 7535
32. Wills, M. Angew. Chem., Int. Ed. 2008, 47, 4264
33. Arita, S.; Koike, T.; Kayaki, Y.; Ikariya, T. Angew. Chem., Int. Ed. 2008, 47, 2447
34. Liu, C.; Xie, J.-H.; Li, Y.-L.; Chen, J.-Q.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2013, 52, 593
35. Yang, X.-H.; Xie, J.-H.; Liu, W.-P.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2013, 52, 7833
36. Kitamura, M.; Kasahara, I.; Manabe, K.; Noyori, R. J. Org. Chem. 1988, 53, 708
37. Cui, P.; Macdonald, T. L.; Chen, M.; Nadler, J. L. Bioorg. Med. Chem. Lett. 2006, 16, 3401
38. Nagasawa, T.; Kuwahara, S. Org. Lett. 2009, 11, 761
39. Pfeiffer, B.; Speck-Gisler, S.; Barandun, L.; Senft, U.; Groot, C.; Lehmann, I.; Ganci, W.; Gertsch, J.; Altmann, K.-H. J. Org. Chem. 2013, 78, 2553
40. Tietze, L. F.; Brasche, G.; Stadler, C.; Grube, A.; Böhnke, N. Angew. Chem., Int. Ed. 2006, 45, 5015
41. MacMillan, J. B.; Molinski, T. F. Org. Lett. 2002, 4, 1535
42. Ramachandran, P. V.; Krzeminski, M. P.; Ram Reddy, M. V.; Brown, H. C. Tetrahedron: Asymmetry 1999, 10, 11
43. Fazio, F.; Schneider, M. P. Tetrahedron Lett. 2002, 43, 811
44. Bringmann, G.; Lang, G.; Michel, M.; Heubes, M. Tetrahedron Lett. 2004, 45, 2829
45. Utaka, M.; Watabu, H.; Takeda, A. J. Org. Chem. 1987, 52, 4363
46. Runmo, A.-B. L.; Pàmies, O.; Faber, K.; Bäckvall, J.-E. Tetrahedron Lett. 2002, 43, 2983
47. Díaz-Rodríguez, A.; Borzecka, W.; Lavandera, I.; Gotor, V. ACS Catal. 2014, 4, 386
48. Xie, J.-H.; Zhou, Q.-L. Acta Chim. Sin. 2014, 72, 778
49. Xie, J.-H.; Liu, X.-Y.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2011, 50, 7329
50. Xie, J.-H.; Liu, X.-Y.; Yang, X.-H.; Xie, J.-B.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2012, 51, 201
51. The value of the selectivity factor s was obtained using Kagan's equation: s = ln[(1-C (1 + ee)]/ln[(1-C (1-ee)], where C is the conversion and ee is the ee value of the product. See: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249
52. Maurer, B.; Grieder, A.; Thommen, W. Helv. Chim. Acta 1979, 62, 44
53. Sultana, S.; Indukuri, K.; Deka, M. J.; Saikia, A. K. J. Org. Chem. 2013, 78, 12182
54. Karlubíková, O.; Babjak, M.; Gracza, T. Tetrahedron 2011, 67, 4980
55. O'Brien, M.; Cahill, S.; Evans, L. A. Chem. Commun. 2008, 5559