Catalytic enantioselective desymmetrization of meso-N-acylaziridines with TMSCN

Journal of the American Chemical Society

Volumn 127, Issue 32, 2005, Pages 11252-11253

  Mita, Tsuyoshi ^a   Fujimori, Ikuo ^a   Wada, Reiko ^a   Wen, Jianfeng ^a   Kanai, Motomu ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; CYANIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLIZATION; CYANATION; ENANTIOMER; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

AMINO ACIDS, CYCLIC; AZIRIDINES; CATALYSIS; CYANIDES; ISOMERISM; TRIMETHYLSILYL COMPOUNDS;

EID: 23844530814     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053486y     Document Type: Article

References (28)

1. (a) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
2. (b) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1.
3. (c) Fülöp, F, Chem Rev. 2001, 101, 2181.
4. (a) Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206.
5. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
6. Diastereoselective reactions using chiral amine derivatives are the main method. For selected examples, see: (a) Enderes, D.; Wiedemann, J.; Bettray, W. Synlett 1995, 369.
7. (b) LePlae, P. R.; Umezawa, N.; Lee, H.-S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629.
8. For enzymatic synthesis, see: Kanerva, L. T.; Csomós, P.; Sundholm, O.; Bernáth, G.; Fülöp, F. Tetrahedron: Asymmetry 1996, 7, 1705.
9. Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, 1999; Vol. III, Chapter 35.
10. Muller, P.; Nury, P. Org. Lett. 1999, 1, 439.
11. Li, Z.; Fernández, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611.
12. For other catalytic enantioselective desymmetrizations of aziridines, see: (a) Zhang, Z. D.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602.
13. (b) Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc., Chem. Commun. 1994, 2699.
14. (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668.
15. (b) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1704.
16. (c) Schaus, S. E.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001.
17. (a) Rowlands, G. J. Tetrahedron 2001, 57, 1865.
18. (b) Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491.
19. (a) Yabu, K.; Masumoto, S.; Yamasaki, S.; Hainashhna, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908.
20. (b) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
21. (c) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147.
22. (d) Mita, T.; Sasaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 514.
23. Other lanthanide metals gave less satisfactory results than Gd. In all entries, the isomeric isonitriles were produced in less than detectable amounts.
24. Addition of HCN instead of DMP produced less satisfactory results (89% yield, 74% ee).
25. See Supporting Information for details.
26. For example, 4d and 4h were obtained with 78 and 82% ee in the absence of TFA (82 and 85% ee in the presence of TFA; see Table 2).
27. The same MS peak was observed in the absence of DMP, which was consistent with the experimental results that DMP did not change the enantioselectivity.
28. For example, see: Yang, X.; Jones, R. A. J. Am. Chem. Soc. 2005, 127, 7686.