A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis

Journal of the American Chemical Society

Volumn 135, Issue 45, 2013, Pages 16849-16852

  Wang, Pan ^a   Tao, Wen Jie ^a   Sun, Xiu Li ^a   Liao, Saihu ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CANNIZZARO REACTION; DYNAMIC KINETIC RESOLUTION; ENANTIOSELECTIVE; ENANTIOSELECTIVE ADDITION; GLYOXAL; HEMIACETAL INTERMEDIATE;

ALDEHYDES;

ENANTIOSELECTIVITY;

1,2 DICHLOROETHANE; ALCOHOL DERIVATIVE; CUPRIC ION; DEUTERIUM; GLYOXAL; NAPHTHALENE; PHENYLGLYOXAL;

ARTICLE; CANNIZZARO REACTION; CATALYSIS; CHEMICAL REACTION KINETICS; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 84887765888     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja409859x     Document Type: Article

References (58)

1. Pechmann, H. v. Ber. Dtsch. Chem. Ges. 1887, 20, 2904
2. Fuson, R. C.; Gray, H.; Gouza, J. J. J. Am. Chem. Soc. 1939, 61, 1937
3. Alexander, E. R. J. Am. Chem. Soc. 1947, 69, 289
4. Salomaa, P. Acta Chem. Scand. 1956, 10, 311
5. Jin, S. J.; Arora, P. K.; Sayre, L. M. J. Org. Chem. 1990, 55, 3011
6. Likhar, P. R.; Bandyopadhyay, A. K. Synlett 2000, 538
7. Abaee, M. S.; Sharifi, R.; Mojtahedi, M. M. Org. Lett. 2005, 7, 5893
8. Curini, M.; Epifano, F.; Genovese, S.; Marcotullio, M. C.; Rosati, O. Org. Lett. 2005, 7, 1331
9. Hayashi, Y.; Sasaki, Y. Chem. Commun. 2005, 2716
10. Wang, Z.-C.; Jiang, Y.-J.; Baiker, A.; Huang, J. Acs Catal 2013, 3, 1573
11. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach; Pergamon: New York, 1983.
12. Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Syntheses; Wiley-VCH: Weinheim, 1997.
13. Yang, J.-W.; List, B. Org. Lett. 2006, 8, 5653
14. Sun, X.-F.; Li, W.; Zhou, L.; Zhang, X.-M. Chem.-Eur. J. 2009, 15, 7302
15. Li, S.; Zhu, S.-F.; Xie, J.-H.; Song, S.; Zhang, C.-M.; Zhou, Q.-L. J. Am. Chem. Soc. 2010, 132, 1172
16. Zhu, S.-F.; Zhou, Q.-L. Acc. Chem. Res. 2012, 45, 1365
17. Maruyama, K.; Murakami, Y.; Yoda, K.; Mashino, T.; Nishinaga, A. J. Chem. Soc., Chem. Commun. 1992, 1617
18. Russell, A. E.; Miller, S. P.; Morken, J. P. J. Org. Chem. 2000, 65, 8381
19. Ishihara, K.; Yano, T.; Fushimi, M. J. Fluorine Chem. 2008, 129, 994
20. An elegant biomimetic approach via dienol mechansim afforded 35% yield and up to 83% ee: Schmitt, E.; Schiffers, I.; Bolm, C. Tetrahedron Lett. 2009, 50, 3185
21. Ghosh, A. K.; Packiarajan, M.; Cappiello, J. Tetrahedron: Asymmetry 1998, 9, 1
22. Desimoni, G.; Faita, G.; Jørgensen, K. A. Chem. Rev. 2011, 111, PR284
23. Foltz, C.; Stecker, B.; Marconi, G.; Bellemin-Laponnaz, S.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2007, 13, 9912
24. Landa, A.; Richter, B.; Johansen, R. L.; Minkkila, A.; Jørgensen, K. A. J. Org. Chem. 2007, 72, 240
25. Singh, P. K.; Bisai, A.; Singh, V. K. Tetrahedron Lett. 2007, 48, 1127
26. Toussaint, A.; Pfaltz, A. Eur. J. Org. Chem. 2008, 4591
27. Hager, M.; Wittmann, S.; Schatz, A.; Pein, F.; Kreitmeier, P.; Reiser, O. Tetrahedron: Asymmetry 2010, 21, 1194
28. Harvey, J. S.; Simonovich, S. P.; Jamison, C. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 13782
29. Bigot, A.; Williamson, A. E.; Gaunt, M. J. J. Am. Chem. Soc. 2011, 133, 13778
30. Nano, A.; Brelot, L.; Rogez, G.; Maisse-Francois, A.; Bellemin-Laponnaz, S. Inorg. Chim. Acta 2011, 376, 285
31. Leboeuf, D.; Gandon, V.; Ciesielski, J.; Frontier, A. J. J. Am. Chem. Soc. 2012, 134, 6296
32. Li, J.; Pan, W.; Wang, Z.; Zhang, X.; Ding, K. Adv. Synth. Catal. 2012, 354, 1980
33. Deng, C.; Wang, L. J.; Zhu, J.; Tang, Y. Angew. Chem., Int. Ed. 2012, 51, 11620
34. Song, X.-G.; Zhu, S.-F.; Xie, X. L.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2013, 52, 2555
35. Xiong, H.; Xu, H.; Liao, S.; Xie, Z.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 7851
36. Zhou, J.; Tang, Y. Chem. Soc. Rev. 2005, 34, 664
37. Bellemin-Laponnaz, S.; Gade, L. H. Actual Chimique 2007, 16
38. Hargaden, G. C.; Guiry, P. J. Chem. Rev. 2009, 109, 2505
39. Zhou, J.; Tang, Y. J. Am. Chem. Soc. 2002, 124, 9030
40. Rasappan, R.; Hager, M.; Gissible, A.; Reiser, O. Org. Lett. 2006, 8, 6099
41. Seitz, M.; Capacchione, C.; Bellemin-Laponnaz, S.; Wadepohl, H.; Ward, B. D.; Gade, L. H. Dalton Trans. 2006, 193
42. Gade, L. H.; Bellemin-Laponnaz, S. Chem.-Eur. J. 2008, 14, 4142
43. Schätz, A.; Rasappan, R.; Hager, M.; Gissibl, A.; Reiser, O. Chem.-Eur. J. 2008, 14, 7259
44. Rendina, V. L.; Moebius, D. C.; Kingsbury, J. S. Org. Lett. 2011, 13, 2004
45. Rendina, V. L.; Kaplan, H. Z.; Kingsbury, J. S. Synthesis 2012, 44, 686
46. Li, J.; Liao, S.-H.; Xiong, H.; Zhou, Y.-Y.; Sun, X.-L.; Zhang, Y.; Zhou, X.-G.; Tang, Y. Angew. Chem., Int. Ed. 2012, 51, 8838
47. Xu, H.; Qu, J.-P.; Liao, S.; Xiong, H.; Tang, Y. Angew. Chem., Int. Ed. 2013, 52, 4004
48. Zhou, Y.-Y.; Li, J.; Ling, L.; Liao, S.-H.; Sun, X.-L.; Li, Y.-X.; Wang, L.-J.; Tang, Y. Angew. Chem., Int. Ed. 2013, 52, 1452
49. Zhou, J.-L.; Wang, L.-J.; Xu, H.; Sun, X.-L.; Tang, Y. ACS Catal. 2013, 3, 685
50. Ohshima, T.; Yamamoto, Y.; Takaki, U.; Inoue, Y.; Saeki, T.; Itou, K.; Maegawa, Y.; Iwasaki, T.; Mashima, K. Chem. Commun. 2009, 2688
51. Knifton, J. F. Tetrahedron Lett. 1975, 2163
52. Knifton, J. F. J. Org. Chem. 1976, 41, 1200
53. Mashima, K.; Kusano, K. H.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizaki, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064
54. Li, Y.-J.; Izumi, T. J. Chin. Chem. Soc. 2002, 49, 505
55. Schabel, T.; Belger, C.; Plietker, B. Org. Lett. 2013, 15, 2858
56. Valls, N.; Vallribera, M.; Carmeli, S.; Bonjoch, J. Org. Lett. 2003, 5, 447
57. Henke, B. R. J. Med. Chem. 2004, 47, 4118
58. Shrestha, S.; Bhattarai, B. R.; Cho, H.; Choi, J. K.; Cho, H. Bioorg. Med. Chem. Lett. 2007, 17, 2728