Auxiliary-controlled asymmetric [3+2]-dipolar cycloaddition of azomethine ylides generated from Au-catalyzed intramolecular redox reaction of nitronyl alkynes

Chemistry - An Asian Journal

Volumn 6, Issue 8, 2011, Pages 1977-1981

  Jeong, Jaewon ^a   Yeom, Hyun Suk ^a   Kwon, Ohyun ^b   Shin, Seunghoon ^a  

^a Hanyang University   (South Korea)

^b Samsung Mobile Display Co   (South Korea)

Author keywords

3+2 dipolar cycloaddition; chiral auxiliaries; gold; hydroxylamines; ylides

Indexed keywords

ALKYNYLS; AZOMETHINE YLIDES; CHIRAL AUXILIARIES; DIPOLAR CYCLOADDITIONS; HYDROXYLAMINES; IN-SITU; NITRONES; YLIDES;

ACETYLENE; AMINES; CYCLOADDITION; REACTION KINETICS; REDOX REACTIONS;

CATALYSIS;

EID: 79961077074     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201100159     Document Type: Article

References (44)

1. I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765.
2. G. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484. N-Coordinating metal catalysts are most widely in use in asymmetric [3+2] dipolar cycloadditions, see
3. L. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887
4. S. Husinec, V. Savic, Tetrahedron: Asymmetry 2005, 16, 2047. For chiral dipolarophiles
5. M. Kissane, A. R. Maguire, Chem. Soc. Rev. 2010, 39, 845. For chiral azomethine ylides, see ref. 5.
6. H. S. Yeom, J. E. Lee, S. Shin, Angew. Chem. 2008, 120, 7148
7. Angew. Chem. Int. Ed. 2008, 47, 7040; For the generation of other reactive intermediates, such as carbene, imine, and enolates, see
8. H. S. Yeom, Y. Lee, J. E. Lee, S. Shin, Org. Biomol. Chem. 2009, 7, 4744
9. H. S. Yeom, Y. Lee, J. Jeong, E. So, S. Hwang, J. E. Lee, S. S. Lee, S. Shin, Angew. Chem. 2010, 122, 1655
10. Angew. Chem. Int. Ed. 2010, 49, 1611. For amine-N-oxide redox reactions
11. L. Cui, G. Zhang, Y. Peng, L. Zhang, Org. Lett. 2009, 11, 1225
12. L. Cui, Y. Peng, L. Zhang, J. Am. Chem. Soc. 2009, 131, 8394
13. L. Ye, L. Cui, G. Zhang, L. Zhang, J. Am. Chem. Soc. 2010, 132, 3258; For sulfur-N-oxide redox reactions
14. N. D. Shapiro, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 4160
15. G. Li, Z. Zhang, Angew. Chem. 2007, 119, 5248
16. Angew. Chem. Int. Ed. 2007, 46, 5156
17. P. W. Davies, S. J. C. Albrecht, Angew. Chem. 2009, 121, 8522
18. Angew. Chem. Int. Ed. 2009, 48, 8372
19. C. W. Li, K. Pati, G. Y. Lin, S. M. A. Sohel, H. H. Hung, R. S. Liu, Angew. Chem. 2010, 122, 10087
20. Angew. Chem. Int. Ed. 2010, 49, 9891.
21. A. Katritzky, Chem. Rev. 1989, 89, 827; For recent applications in synthesis, see
22. K. M. Peese, D. Y. Gin, Chem. Eur. J. 2008, 14, 1654.
23. A. Padwa, Y. Y. Chen, U. Chiacchio, W. Dent, Tetrahedron 1985, 41, 3529
24. J. Rouden, J. Royer, H. P. Husson, Tetrahedron Lett. 1989, 30, 5133
25. P. Deprez, J. Royer, H. P. Husson, Tetrahedron: Asymmetry 1991, 2, 1189
26. P. Garner, W. B. Ho, S. K. Grandhee, W. J. Young, V. O. Kennedy, J. Org. Chem. 1991, 56, 5893. Conformationally rigid cyclic azomethine ylides
27. R. M. Williams, W. Zhai, D. J. Aldous, S. C. Aldous, J. Org. Chem. 1992, 57, 6527. For chiral azomethine ylides in an intramolecular cycloadditions
28. P. Garner, K. Sunitha, W. B. Ho, W. J. Young, V. O. Kennedy, A. Djebli, J. Org. Chem. 1989, 54, 2041
29. R. C. F. Jones, K. J. Howard, J. S. Snaith, Tetrahedron Lett. 1997, 38, 1647
30. L. M. Harwood, I. A. Lilley, Tetrahedron Lett. 1993, 34, 537
31. M. G. Drew, L. M. Harwood, D. W. Price, M. S. Choi, G. Park, Tetrahedron Lett. 2000, 41, 5077.
32. R. A. Widenhoefer, Chem. Eur. J. 2008, 14, 5382
33. II-catalyzed asymmetric dipolar cycloaddition was reported by N. Iwasawa
34. K. Ishida, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2010, 132, 8842.
35. H. Tokuyama, T. Kuboyama, A. Amano, T. Yamashita, T. Fukuyama, Synthesis 2000, 1299
36. T. Fukuyama, T. Kuboyama, H. Tokyuama, Org. Synth. 2003, 80, 207
37. J. W. Bode, R. M. Fox, K. D. Baucom, Angew. Chem. 2006, 118, 1270
38. Angew. Chem. Int. Ed. 2006, 45, 1248.
39. M. Chérest, H. Felkin, N. Prudent, Tetrahedron Lett. 1968, 9, 2199
40. N. T. Anh, O. Eisenstein, Nouv. J. Chim. 1977, 1, 61.
41. A. D. Becke, J. Chem. Phys. 1993, 98, 5648
42. W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley, New York, 2000
43. R. G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, Oxford, 1989
44. Gaussian 03, Revision D.02, M. J. Frisch et al., Gaussian, Inc., Pittsburgh, PA, 2004 (Full reference given in the Supporting Information).