Aziridinyl vinyl ketones from the asymmetric catalytic aziridination reaction

European Journal of Organic Chemistry

Volumn , Issue 13, 2007, Pages 2068-2071

  Deng, Yonghong ^a   Young, Rok Lee ^a   Newman, Cory A ^a   Wulff, William D ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Aziridines; Lewis acids

Indexed keywords

EID: 34250658953     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601126     Document Type: Article

References (17)

1. H. A. Albar, Journal of King Abdulaziz University 1999, 11, 65;
2. Chem. Abstr. 2001, 134, 340471.
3. a) J. C. Antilla, W. D. Wulff, J. Am. Chem. Soc. 1999, 121, 5099;
4. b) J. C. Antilla, W. D. Wulff, Angew. Chem. Int. Ed. 2000, 39, 4518;
5. c) C. Loncaric, W. D. Wulff, Org. Lett. 2001, 3, 3675;
6. d) A. P. Patwardan, V. R. Pulgam, Y. Zhang, W. D. Wulff, Angew. Chem. Int. Ed. 2005, 44, 6169.
7. a) For solid-state structures of the vapol ligand, see: C. P. Price, A. J. Matzger, J. Org. Chem. 2005, 70, 1;
8. b) For platinum complexes of vanol and vapol, see: J. J. Becker, J. J. P. S. White, M. R. Gagné, Organometallics 2003, 22, 3245.
9. a) J. Bao, W. D. Wulff, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 3814;
10. b) D. P. Heller, D. R. Goldberg, W. D. Wulff, J. Am. Chem. Soc. 1997, 119, 10551;
11. c) D. P. Heller, D. R. Goldberg, H. Wu, Hongqiao, W. D. Wulff, Can. J. Chem. 2006, 84, 0000.
12. S. Xue, S. Yu, Y. Deng, W. D. Wulff, Angew. Chem. Int. Ed. 2001, 40, 2271.
13. C. Bolm, J.-C. Frison, Y. Zhang, W. D. Wulff, Synlett 2004, 1619.
14. J. Bao, W. D. Wulff, Tetrahedron Lett. 1995, 36, 3321.
15. R. L. Danheiser, R. F. Miller, R. G. Brisbois, Org. Synth. 1996, 73, 134.
16. J. M. Yun, T. B. Sim, H. S. Hahm, W. K. Lee, J. Org. Chem. 2003, 68, 7675.
17. The relative stereochemistry of 14 was determined by X-ray diffraction analysis on its para-nitrobenzoyl derivative, see Supporting Information.