Multicomponent catalytic asymmetric aziridination of aldehydes

Organic Letters

Volumn 13, Issue 21, 2011, Pages 5866-5869

  Gupta, Anil K ^a   Mukherjee, Munmun ^a   Wulff, William D ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AZIRIDINE; AZIRIDINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; AZIRIDINES; CATALYSIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 80055099878     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202472z     Document Type: Article

References (28)

1. Guillena, G.; Ramon, D. J.; Yus, M. Tetrahedron: Asymmetry 2007, 18, 693-700
2. Ramon, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602-1634
3. Multicomponent Reactions; Zhu, J.; Bienayme, H., Eds.; Wiley-VCH: 2005.
4. Pellissier, H. Tetrahedron 2010, 66, 1509
5. Nagayama, S.; Kobayashi, S. Chem. Lett. 1998, 685-686
6. Kubo, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 625-626
7. Yadav, J. S.; Reddy, B. V. S.; Rao, M. S.; Reddy, P. N. Tetrahedron Lett. 2003, 44, 5275-5278
8. Yadav, J. S.; Reddy, B. V. S.; Reddy, P. N.; Rao, M. S. Synthesis 2003, 1387-1390
9. Ishii, Y.; Sakaguchi, S. Bull. Chem. Soc. Jpn. 2004, 77, 909-920
10. For a sequential component aziridination with a chiral catalyst, see: Akiyama, T.; Suzuki, T.; Mori, K. Org. Lett. 2009, 11, 2445-2447
11. Minakata, S.; Ando, T.; Nishimura, M.; Ryu, I.; Komatsu, M. Angew. Chem., Int. Ed. 1998, 37, 3392-3394
12. Nishimura, M.; Minakata, S.; Takahashi, T.; Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2002, 67, 2101-2110
13. Zhang, Y.; Desai, A.; Lu, Z.; Hu, G.; Ding, Z.; Wulff, W. D. Chem. Eur. J. 2008, 14, 3785-3803
14. Zhang, Y.; Lu, Z.; Desai, A.; Wulff, W. D. Org. Lett. 2008, 8, 5429-5432
15. Zhang, Y.; Lu, Z.; Wulff, W. D. Synlett 2009, 2715-2739
16. Hu, G.; Huang, L.; Huang, R. H.; Wulff, W. D. J. Am. Chem. Soc. 2009, 131, 15615-15617
17. Mukherjee, M.; Gupta, A. K.; Lu, Z.; Zhang, Y.; Wulff, W. D. J. Org. Chem. 2010, 75, 5643-5660
18. Desai, A. A.; Wulff, W. D. J. Am. Chem. Soc. 2010, 132, 13100-13103
19. Vetticatt, M. J.; Desai, A. A.; Wulff, W. D. J. Am. Chem. Soc. 2010, 132, 13104-13107
20. Ren, H.; Wulff, W. D. Org. Lett. 2010, 12, 4908-4911
21. Hu, G.; Gupta, A. K.; Huang, R. H.; Mukherjee, M.; Wulff, W. D. J. Am. Chem. Soc. 2010, 132, 14669-14675
22. Wulff, W. D.; Antilla, J. A.; Pulgam, V. R.; Zhang, Y.; Gilson-Osminksi, W. Unpublished results.
23. Ismail, F. M. D.; Levitsky, D. O.; Dembitsky, V. M. Eur. J. Med. Chem. 2009, 44, 3373 and references therein.
24. Kabara, J. J.; Vrable, R.; Lie Ken Jie, M. S. F. Lipids 1977, 12, 753-759
25. Metzger, J. O.; Fürmeier, S. Eur. J. Org. Chem. 1999, 661-664
26. Falck, J. R.; Manna, S.; Viala, J.; Siddhanta, A. K.; Moustakis, C. A.; Capdevila, J. Tetrahedron Lett. 1985, 26, 2287-2290
27. We have compared the preparation of aziridine 19r by the MCAZ method described here with that of a two-step method involving the isolation of the imine from aldehyde 4r and amine 12. Substantial material loss is encountered in the two-step method as a result of purification of the imine (see Supporting Information).
28. Pyridine-3-carboxaldehyde gave no aziridine (not shown).