Organocatalyzed α-oxyamination of aldehydes using anodic oxidation

European Journal of Organic Chemistry

Volumn , Issue 31, 2009, Pages 5309-5312

  Bui, Nhat Nguyen ^a   Ho, Xuan Huong ^a   Mho, Sun Il ^a   Jang, Hye Young ^a  

^a Ajou University   (South Korea)

Author keywords

Cyclic voltammetry; Enamines; Organocatalysis; Oxidation; Oxyamination

Indexed keywords

EID: 70450202281     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900871     Document Type: Article

References (29)

1. a) H. Maeda, H. Ohmori, Acc. Chem. Res. 1999, 32, 72-80;
2. b) R. D. Little, K. D. Moeller, Interface 2002, 11(4), 36-42;
3. c) Y. Roh, H.-Y. Jang, V. Lynch, N. L. Bauld, M. J. Krische, Org. Lett. 2002, 4, 611-613;
4. d) J. B. Sperry, D. L. Wright, Chem. Soc. Rev. 2006, 35, 605-621;
5. e) H. J. Schäfer, M. Harenbrock, E. Klocke, M. Plate, A. Weiper-Idelmann, Pure Appl. Chem. 2007, 79, 2047-2057;
6. f) A. Jutand, Chem. Rev. 2008, 108, 2300-2347;
7. g) J.-i. Yoshida, K. Kataoka, R. Horcajada, A. Nagaki, Chem. Rev. 2008, 108, 2265-2299 and references cited therein.
8. a) A. K. Vijh, B. E. Conway, Chem. Rev. 1967, 67, 623-664;
9. b) K. D. Moeller, Tetrahedron 2000, 56, 9527-9554 and references cited therein.
10. G. Bareletta, A. C. Chung, C. B. Rios, F. Jordan, J. M. Schlegel, J. Am. Chem. Soc. 1990, 112, 8144-8149.
11. M. Schämann, H. J. Schäfer, Electrochim. Acta 2005, 50, 4956-4972.
12. M. P. Sibi, M. Hasegawa, J. Am. Chem. Soc. 2007, 129, 4124-4125.
13. a) T. B. Beeson, A. Mastracchio, J.-B. Hong, K. Ashton, D. W. C. MacMillan, Science 2007, 316, 582-585;
14. b) H.-Y. Jang, J.-B. Hong, D. W. C. MacMillan, J. Am. Chem. Soc. 2007, 129, 7004-7005;
15. c) H. Kim, D. W. C. MacMillan, J. Am. Chem. Soc. 2008, 130, 398-399.
16. R. Barhdadi, C. Comminges, A. P. Doherty, J. Y. Nédélec, S. O'Toole, M. Troupel, J. Appl. Electrochem. 2007, 37, 723-728.
17. Selected articles on enantioselective electrocatalytic reactions: a) P. Guo, K.-Y. Wong, Electrochem. Commun. 1999, 1, 559-563;
18. b) H. Tanaka, M. Kuroboshi, H. Takeda, H. Kanda, S. Torii, J. Electroanal. Chem. 2001, 507, 75-81;
19. c) P. C. B. Page, F. Marken, C. Williamson, Y. Chan, B. R. Buckley, D. Bethell, Adv. Synth. Catal. 2008, 350, 1149-1154.
20. Selected articles on N-oxyl radical-mediated enantioselective electrocatalytic reactions: a) Y. Kashiwagi, F. Jurashima, C. Kikuchi, J.-i. Anzai, T. Osa, J. M. Bobbit, Chem. Commun. 1999, 1983-1984;
21. b) Y. Kashiwagi, F. Jurashima, C. Kikuchi, J.-i. Anzai, T. Osa, J. M. Bobbit, Tetrahedron Lett. 1999, 40, 6469-6472;
22. c) M. Kuroboshi, H. Yoshihisa, M. N. Cortona, Y. Kawakami, Z. Gao, H. Tanaka, Tetrahedron Lett. 2000, 41, 8131-8135.
23. a) L. L. Miller, J. Org. Chem. 1972, 37, 916-918;
24. b) B. Barbier, J. Pinson, G. Desarmot, M. Sanchez, J. Electrochem. Soc. 1990, 137, 1757-1764;
25. c) R. S. Deinhammer, M. Ho, J. W. Anderegg, M. D. Porter, Langmuir 1994, 10, 1306-1313;
26. d) T. Luczak, J. Appl. Electrochem. 2008, 38, 43-50.
27. T. Shono, Y. Matsumura, H. Hamaguchi, Bull. Chem. Soc. Jpn. 1978, 51, 2179-2180.
28. a) T. Takata, Y. Tsujino, S. Nakanishi, K. Nakamura, E. Yoshida, T. Endo, Chem. Lett. 1999, 937-938;
29. b) T. Ren, Y.-C. Liu, Q.-X. Guo, Bull. Chem. Soc. Jpn. 1996, 69, 2935-2941.