Double nucleophilic addition of ketene silyl (thio)acetals and trimethylsilyl cyanide to α,β-unsaturated aldimines promoted by aluminum chloride

Chemistry Letters

Volumn 32, Issue 7, 2003, Pages 606-607

  Shimizu, Makoto ^a   Kamiya, Makiko ^a   Hachiya, Iwao ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALUMINUM CHLORIDE; CYANIDE; KETENE DERIVATIVE; SILANE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0141540678     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.606     Document Type: Article

References (23)

1. a) A. Strecker, Liebigs Ann., 75, 27 (1850).
2. b) A. Strecker, Liebigs Ann., 91, 349 (1854).
3. c) For a review: G. C. Barrett, "Chemistry and Biochemistry of the Amino Acids," Chapman and Hall, New York (1985), p 251 and 261.
4. I. Ojima, S. Inaba, and K. Nakatsugawa, Chem. Lett., 1975, 331.
5. a) F. A. Davis, R. E. Reddy, and P. S. Portonovo, Tetrahedron Lett., 35, 9351 (1994).
6. b) F. A. Davis, P. S. Portonovo, R. E. Reddy, and Y.-h. Chiu, J. Org. Chem., 61, 440 (1996).
7. c) M. S. Iyer, K. M. Gigstad, N. D. Namdev, and M. Lipton, J. Am. Chem. Soc., 118, 4910 (1996).
8. d) M. S. Sigman and E. N. Jacobsen, J. Am. Chem. Soc., 120, 5315 (1998).
9. e) M. S. Sigman and E. N. Jacobsen, J. Am. Chem. Soc., 120, 4901 (1998).
10. f) H. Ishitani, S. Komiyama, and S. Kobayashi, Angew. Chem., Int. Ed., 37, 3186 (1998).
11. g) C. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, and A. H. Hoveyda, J. Am. Chem. Soc., 121, 4284 (1999).
12. h) J. R. Porter, W. G. Wirschun, K. W. Kuntz, M. L. Snapper, and A. H. Hoveyda, J. Am. Chem. Soc., 122, 2657 (2000).
13. i) M. Takamura, Y. Hamashima, H. Usuda, M. Kanai, and M. Shibasaki, Angew. Chem., Int. Ed., 39, 1650 (2000).
14. j) E. J. Corey and M. J. Grogan, Org. Lett., 1, 157 (2000).
15. a) T. K. Chakraborty, G. V. Reddy, and K. A. Hussain, Tetrahedron Lett., 32, 7597 (1991).
16. b) J. Leblanc and H. W. Gibson, Tetrahedron Lett., 33, 6295 (1992).
17. c) S. Kobayashi, H. Ishitani, and M. Ueno, Synlett, 1997, 115.
18. d) H. Ishitani, S. Komiyama, Y. Hasegawa, and S. Kobayashi, J. Am. Chem. Soc., 122, 762 (2000).
19. a) M. Shimizu, A. Morita, and T. Kaga, Tetrahedron Lett., 40, 8401 (1999).
20. b) M. Shimizu, T. Ogawa, and T. Nishi, Tetrahedron Lett., 42, 5463 (2001).
21. c) M. Shimizu and T. Nishi, Chem. Lett., 2002, 46.
22. It has been reported that several 1,4-addition products derived from α,β-unsaturated imines are readily hydrolyzed to the parent carbonyl compounds. See, M. D. Stadnichuk, A. V. Khramchikhin, Y. L. Piterskaya, and I. V. Suvorova, Russ. J. Gen. Chem., 69, 593 (1999).
23. 1H NMR (NOESY) spectra indicated the relative stereochemistry.