Metal-free, organocatalytic syn diacetoxylation of alkenes

Organic Letters

Volumn 14, Issue 13, 2012, Pages 3336-3339

  Zhong, Wenhe ^a   Liu, Shan ^a   Yang, Jun ^a   Meng, Xiangbao ^a   Li, Zhongjun ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ESTER; IODINATED HYDROCARBON;

ACETYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETYLATION; ALKENES; CATALYSIS; ESTERS; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84863618156     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301311e     Document Type: Article

References (63)

1. Bataille, C. J. R.; Donohoe, T. J. Chem. Soc. Rev. 2011, 40, 114
2. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973
3. Schroder, M. Chem. Rev. 1980, 80, 187
4. Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroeder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968
5. Finn, M. G.; Sharpless, K. B. J. Am. Chem. Soc. 1991, 113, 113
6. Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483
7. Salvador, J. A. R.; Silvestre, S. M.; Moreira, V. M. Curr. Org. Chem. 2008, 12, 492
8. Ho, C.-M.; Yu, W.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2004, 43, 3303
9. Plietker, B.; Niggemann, A.; Pollrich, A. Org. Biomol. Chem. 2004, 2, 1116
10. Yip, W.-P.; Yu, W.-Y.; Zhu, N.; Che, C.-M. J. Am. Chem. Soc. 2005, 127, 14239
11. Yip, W.-P.; Ho, C.-M.; Zhu, N.; Lau, T.-C.; Che, C.-M. Chem.-Asian J. 2008, 3, 70
12. Plietker, B.; Neisius, N. M. J. Org. Chem. 2008, 73, 3218
13. Brinksma, J.; Schmieder, L.; van Vliet, G.; Boaron, R.; Hage, R.; De Vos, D. E.; Alsters, P. L.; Feringa, B. L. Tetrahedron Lett. 2002, 43, 2619
14. de Boer, J. W.; Brinksma, J.; Browne, W. R.; Meetsma, A.; Alsters, P. L.; Hage, R.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 7990
15. Chow, T. W.-S.; Liu, Y.; Che, C.-M. Chem. Commun. 2011, 11204
16. Suzuki, K.; Oldenburg, P. D.; Que, L., Jr. Angew. Chem., Int. Ed. 2008, 47, 1887
17. Companye, A.; Gómez, L.; Fontrodona, X.; Ribas, X.; Costas, M. Chem.-Eur. J. 2008, 14, 5727
18. Bruijnincx, P. C. A.; Buurmans, I. L. C.; Gosiewska, S.; Moelands, M. A. H.; Lutz, M.; Spek, A. L.; van Koten, G.; Klein Gebbink, R. J. M. Chem.-Eur. J. 2008, 14, 1228
19. Bautz, J.; Comba, P.; Lopez de Laorden, C.; Menzel, M.; Rajaraman, G. Angew. Chem., Int. Ed. 2007, 46, 8067
20. Chow, T. W.-S.; W, E. L.-M.; Guo, Z.; Liu, Y.; Huang, J.-S.; Che, C.-M. J. Am. Chem. Soc. 2010, 132, 13229
21. Oldenburg, P. D.; Feng, Y.; Pryjomska-Ray, I.; Ness, D.; Que, L., Jr. J. Am. Chem. Soc. 2010, 132, 17713
22. Li, Y.; Song, D.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2962
23. Wang, A.; Jiang, H.; Chen, H. J. Am. Chem. Soc. 2009, 131, 3846
24. Wang, W.; Wang, F.; Shi, M. Organometallics 2010, 29, 928
25. Park, C. P.; Lee, J. H.; Yoo, K. S.; Jung, K. W. Org. Lett. 2010, 12, 2450
26. Zhu, M.-K.; Zhao, J.-F.; Loh, T.-P. J. Am. Chem. Soc. 2010, 132, 6284
27. Wang, A.; Jiang, H. J. Org. Chem. 2010, 75, 2321
28. Santi et al. developed a novel olefin dihydroxylation catalyzed by diphenyl diselenide, but the diastereoselectivity was dependent on the substrate: Santoro, S.; Santi, C.; Sabatini, M.; Testaferri, L.; Tiecco, M. Adv. Synth. Catal. 2008, 350, 2881
29. Schwarz, M.; Reiser, O. Angew. Chem., Int. Ed. 2011, 50, 10495
30. Emmanuvel, L.; Ali Shaikh, T. M.; Sudalai, A. Org. Lett. 2005, 7, 5071
31. Griffith, J. C.; Jones, K. M.; Picon, S.; Rawling, M. J.; Kariuki, B. M.; Campbell, M.; Tomkinson, N. C. O. J. Am. Chem. Soc. 2010, 132, 14409
32. Yuan, C.; Axelrod, A.; Varela, M.; Danysh, L.; Siegel, D. Tetrahedron Lett. 2011, 52, 2540
33. Jones, K. M.; Tomkinson, N. C. O. J. Org. Chem. 2012, 77, 921
34. Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656
35. Richardson, R. D.; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402
36. Ochiai, M. Chem. Rec. 2007, 7, 12
37. Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299
38. Ochiai, M.; Miyamoto, K. Eur. J. Org. Chem. 2008, 4229
39. Dohi, T.; Kita, Y. Chem. Commun. 2009, 2073
40. Uyanik, M.; Ishihara, K. Chem. Commun. 2009, 2086
41. Pouységu, L.; Deffieux, D.; Quideau, S. Tetrahedron 2010, 66, 2235
42. Zhdankin, V. V. J. Org. Chem. 2011, 76, 1185
43. Celik, M.; Alp, C.; Coskun, B.; Gultekin, M. S.; Balci, M. Tetrahedron Lett. 2006, 47, 3659
44. Shu, X.-Z.; Xia, X.-F.; Yang, Y.-F.; Ji, K.-G.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2009, 74, 7464
45. Kang, Y.-B.; Gade, L. H. J. Am. Chem. Soc. 2011, 133, 3658
46. Fujita, M.; Wakita, M.; Sugimura, T. Chem. Commun. 2011, 3983
47. Zhong, W.; Yang, J.; Meng, X.; Li, Z. J. Org. Chem. 2011, 76, 9997
48. Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244
49. Dohi, T.; Maruyama, A.; Yoshimura, M.; Morimoto, K.; Tohma, H.; Kita, Y. Angew. Chem., Int. Ed. 2005, 44, 6193
50. Sheng, J.; Li, X.; Tang, M.; Gao, B.; Huang, G. Synthesis 2007, 1165
51. Altermann, S. M.; Richardson, R. D.; Page, T. K.; Schmidt, R. K.; Holland, E.; Mohammed, U.; Paradine, S. M.; French, A. N.; Richter, C.; Bahar, A. M.; Witulski, B.; Wirth, T. Eur. J. Org. Chem. 2008, 5315
52. Miyamoto, K.; Sei, Y.; Yamaguchi, K.; Ochiai, M. J. Am. Chem. Soc. 2009, 131, 1382
53. Uyanik, M.; Akakura, M.; Ishihara, K. J. Am. Chem. Soc. 2009, 131, 251
54. Quideau, S.; Lyvinec, G.; Marguerit, M.; Bathany, K.; Ozanne-Beaudenon, A.; Buffeteau, T.; Cavagnat, D.; Chénedé, A. Angew. Chem., Int. Ed. 2009, 48, 4605
55. Uyanik, M.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2010, 49, 2175
56. Ngatimin, M.; Frey, R.; Andrews, C.; Lupton, D. W.; Hutt, O. E. Chem. Commun. 2011, 11778
57. Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605
58. Rodríguez, A.; Moran, W. J. Org. Lett. 2011, 13, 2220
59. Miyamoto, K.; Sakai, Y.; Goda, S.; Ochiai, M. Chem. Commun. 2012, 982
60. Plesnicar, B. Oxidations in Organic Chemistry; Trahanovsky, W. S., Ed.; Academic Press: New York, 1978; Part C, p 211.
61. Kang, Y.-B.; Gade, L. H. J. Org. Chem. 2012, 77, 1610
62. Usui, Y.; Sato, K.; Tanaka, M. Angew. Chem., Int. Ed. 2003, 42, 5623
63. Rosatellaa, A. A.; Afonsoa, C. A. M. Adv. Synth. Catal. 2011, 353, 2920