Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones

Chemical Communications

Volumn 48, Issue 11, 2012, Pages 1698-1700

  Chen, Mu Wang ^a   Chen, Qing An ^a   Duan, Ying ^a   Ye, Zhi Shi ^a   Zhou, Yong Gui ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3 BUTYL 3 HYDROXYISOINDOLIN 1 ONE; 3 SUBSTITUTED 3 HYDROXYISOINDOLIN 1 ONE DERIVATIVE; ALCOHOL DERIVATIVE; ESTER DERIVATIVE; HANTZSCH ESTER; HYDROGEN; PHOSPHORIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; HYDROGENOLYSIS; SYNTHESIS; TAUTOMERIZATION;

EID: 84863012114     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc16832d     Document Type: Article

References (83)

1. C. Rüchardt, M. Gerst, J. Ebenhoch, Angew. Chem. Int. Ed. 1997, 36, 1406
2. Z. Yuan, L. Wang, J. Wang, S. Xia, P. Chen, Z. Hou, X. Zheng, Appl. Catal. B 2011, 101, 431
3. H. Mao, X. Liao, B. Shi, Catal. Commun. 2011, 12, 1177
4. G. Zhong, B. Chan, L. Radom, Org. Lett. 2009, 11, 749
5. E. Negishi and A. De Meiiere, Handbook of Organopalladium Chemistry for Organic Synthesis, John Wiley & Sons, Inc. Press, New York, 2002, p. 3424
6. R. D. Nimmagadda, C. McRae, Tetrahedron Lett. 2006, 47, 5755
7. M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, Tetrahedron Lett. 2009, 50, 5930
8. D. Coll, F. Delbecq, Y. Aray, P. Sautet, Phys. Chem. Chem. Phys. 2011, 13, 1448
9. R. M. Bullock, Chem.–Eur. J. 2004, 10, 2366
10. R. J. Rahaim Jr, R. E. Maleczka Jr, Org. Lett. 2010, 13, 584
11. A. G. Sergeev, J. F. Hartwig, Science 2011, 332, 439
12. G. A. Olah, A.-H. Wu, O. Farooq, J. Org. Chem. 1988, 53, 5143
13. G. A. Olah, Q. Wu, G. K. S. Prakash, Synlett 1992, 647
14. M. Periasamy, M. Thirumalaikumar, J. Organomet. Chem. 2000, 609, 137
15. E. Dieter, D. Eric, Tetrahedron Lett. 2000, 41, 2347
16. E. Deniau, D. Enders, Tetrahedron 2001, 57, 2581
17. E.-C. Wang, H.-F. Chen, P.-K. Feng, Y.-L. Lin, M.-K. Hsu, Tetrahedron Lett. 2002, 43, 9163
18. C. Sánchez-Sánchez, E. Pére-Inestrosa, R. García-Segura, R. Suau, Tetrahedron 2002, 58, 7267
19. J. Shi, H. Shigehisa, C. A. Guerrero, R. A. Shenvi, C.-C. Li, P. S. Baran, Angew. Chem. Int. Ed. 2009, 48, 4328
20. Y. Chen, W. Tang, J. Mou, Z. Li, Angew. Chem. Int. Ed. 2010, 49, 5278
21. M. G. Bursavich, C. W. West, D. H. Rich, Org. Lett. 2001, 3, 2317
22. D. Díaz, V. S. Martín, Org. Lett. 2000, 2, 335
23. B. Wang, Y. Tu, Acc. Chem. Res. 2011, 44, 1207
24. T. Liang, Z. Zhang, J. C. Antilla, Angew. Chem. Int. Ed. 2010, 49, 9734
25. G. K. S. Prakash, T. Mathew, E. R. Marinez, P. M. Esteves, G. Rasul, G. A. Olah, J. Org. Chem. 2006, 71, 3952
26. K. Prantz, J. Mulzer, Chem. Rev. 2010, 110, 3741
27. C. Waterlot, D. Couturier, M. De Backer, B. Rigo, Can. J. Chem. 2000, 78, 1242
28. M. Schlaf, P. Ghosh, P. Fagan, E. Hauptman, R. M. Bullock, Angew. Chem. Int. Ed. 2001, 40, 3887
29. E. L. Myers, J. G. De Vries, V. K. Aggarwal, Angew. Chem. Int. Ed. 2007, 46, 1893
30. I. T. Raheem, P. S. Thiara, E. A. Peterson, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 13404
31. D. J. Mergott, S. J. Zuend, E. N. Jacobsen, Org. Lett. 2008, 10, 745
32. I. T. Raheem, P. S. Thiara, E. N. Jacobsen, Org. Lett. 2008, 10, 1577
33. E. A. Peterson, E. N. Jacobsen, Angew. Chem. Int. Ed. 2009, 48, 6328
34. M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 10796
35. R. M. de Figueiredo, M. Christmann, Eur. J. Org. Chem. 2007, 2575
36. M. Rueping, B. J. Nachtsheim, Synlett 2010, 119
37. X. L. Yu, A. D. Lu, Y. M. Wang, G. P. Wu, H. B. Song, Z. H. Zhou, C. C. Tang, Eur. J. Org. Chem. 2011, 892
38. X. L. Yu, Y. M. Wang, G. P. Wu, H. B. Song, Z. H. Zhou, C. C. Tang, Eur. J. Org. Chem. 2011, 3060
39. S. G. Ouellet, A. M. Walji, D. W. C. Macmillan, Acc. Chem. Res. 2007, 40, 1327
40. S.-L. You, Chem.–Asian J. 2007, 2, 820
41. S. J. Connon, Org. Biomol. Chem. 2007, 5, 3407
42. C. Wang, X. F. Wu, J. L. Xiao, Chem.–Asian J. 2008, 3, 1750
43. M. Rueping, E. Sugiono, F. R. Schoepke, Synlett 2010, 852
44. M. Rueping, J. Dufour, F. R. Schoepke, Green Chem. 2011, 13, 1084
45. M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781
46. S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. Int. Ed. 2005, 44, 7424
47. R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84
48. S. Hoffmann, M. Nicoletti, B. List, J. Am. Chem. Soc. 2006, 128, 13074
49. T. Akiyama, Chem. Rev. 2007, 107, 5744
50. M. Terada, Chem. Commun. 2008, 4097
51. Q. Kang, Z.-A. Zhao, S.-L. You, Org. Lett. 2008, 10, 2031
52. Q.-S. Guo, D.-M. Du, J. Xu, Angew. Chem. Int. Ed. 2008, 47, 759
53. M. Rueping, T. Theissmann, S. Raja, J. W. Bats, Adv. Synth. Catal. 2008, 350, 1001
54. T. B. Nguyen, H. Bousserouel, Q. Wang, F. Guéritte, Org. Lett. 2010, 12, 4705
55. M. Rueping, C. Brinkmann, A. P. Antonchick, I. Atodiresei, Org. Lett. 2010, 12, 4604
56. T. B. Nguyen, H. Bousserouel, Q. Wang, F. Guéritte, Adv. Synth. Catal. 2011, 353, 257
57. Q.-A. Chen, D.-S. Wang, Y.-G. Zhou, Y. Duan, H.-J. Fan, Y. Yang, Z. Zhang, J. Am. Chem. Soc. 2011, 133, 6126
58. Q.-A. Chen, M.-W. Chen, C.-B. Yu, L. Shi, D.-S. Wang, Y. Yang, Y.-G. Zhou, J. Am. Chem. Soc. 2011, 133, 16432
59. V. N. Wakchaure, M. Nicoletti, L. Ratjen, B. List, Synlett 2010, 2708
60. V. N. Wakchaure, J. Zhou, S. Houffmann, B. List, Angew. Chem. Int. Ed. 2010, 49, 4612
61. C. Zhu, T. Akiyama, Org. Lett. 2009, 11, 4180
62. C. Zhu, T. Akiyama, Adv. Synth. Catal. 2010, 352, 1846
63. D. Enders, J. X. Liebich, G. Raaabe, Chem.–Eur. J. 2010, 16, 9763
64. A. Henseler, M. Kato, K. Mori, T. Akiyama, Angew. Chem. Int. Ed. 2011, 50, 8180
65. T. R. Belliotti, W. A. Brink, S. R. Kesten, J. R. Rubin, D. J. Wustrow, K. T. Zoski, S. Z. Whetzel, A. E. Corbin, T. A. Pugsley, T. G. Heffner, L. D. Wise, Bioorg. Med. Chem. Lett. 1998, 8, 1499
66. T. Wada, N. Fukuda, Psychopharmacology 1991, 103, 314
67. T. L. Stuk, B. K. Assink, R. C. Bates, D. T. Erdman Jr, V. Fedij, S. M. Jennings, J. A. Lassing, R. J. Smith, T. L. Smith, Org. Process Res. Dev. 2003, 7, 851
68. J. R. Fuchs, R. L. Funk, Org. Lett. 2001, 3, 3923
69. R. Grigg, M. J. R. Dorrity, J. F. Malone, T. Mongkolaus-savaratana, W. D. J. A. Norbert, V. Sridharan, Tetrahedron Lett. 1990, 31, 3075
70. D. Enders, V. Braig, G. Raabe, Can. J. Chem. 2001, 79, 1528
71. J. Clayden, C. J. Menet, Tetrahedron Lett. 2003, 44, 3059
72. L. Shen, R. P. Hsung, Org. Lett. 2005, 7, 775
73. J. Pérard-Viret, T. Prangé, A. Tomas, J. Royer, Tetrahedron 2002, 58, 5103
74. D. L. Comins, S. Schilling, Y. Zhang, Org. Lett. 2005, 7, 95
75. M. Lamblin, A. Couture, E. Deniau, P. Grandclaudon, Tetrahedron: Asymmetry 2008, 19, 111
76. S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1997, 38, 3627
77. S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1999, 40, 141
78. S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1999, 40, 143
79. S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, J. Chem. Soc. Perkin Trans. 1 2000, 1715
80. E. Deniau, D. Enders, A. Couture, P. Grandclaudon, Tetrahedron: Asymmetry 2003, 14, 2253
81. A. A. Bahajaj, J. M. Vernon, G. D. Wilson, Tetrahedron 2004, 60, 1247
82. M.-D. Chen, X. Zhou, M.-Z. He, Y.-P. Ruan, P.-Q. Huang, Tetrahedron 2004, 60, 1651
83. E. Deniau, A. Couture, P. Grandclaudon, Tetrahedron: Asymmetry 2008, 19, 2735