"N-acyliminium ion pool" as a heterodiene in [4 + 2] cycloaddition reaction

Organic Letters

Volumn 5, Issue 6, 2003, Pages 945-947

  Suga, Seiji ^a   Nagaki, Aiichiro ^a   Tsutsui, Yamato ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; ALKENE DERIVATIVE; ALKYL GROUP; ALKYNE; CATION; ION; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CALCULATION; CYCLOADDITION; NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS; X RAY ANALYSIS;

EID: 0141739312     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0341243     Document Type: Article

References (34)

1. Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
2. Weinreb, S. M.; Scola, P. M. Chem. Rev. 1989, 89, 1525.
3. Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652. See also: Schmidt, R. R.; Hoffmann, A. R. Chem. Ber. 1974, 107, 78.
4. Tomazela, D. M.; Moraes, L. A. B.; Pilli, R. A.; Eberlin, M. N.; D'Oca, M. G. M. J. Org. Chem. 2002, 67, 4652. See also: Schmidt, R. R.; Hoffmann, A. R. Chem. Ber. 1974, 107, 78.
5. Esch, P. M.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1992, 48, 3445.
6. (a) Zaugg, H. E.; Martin, W. B. Org. React. 1965, 14, 52.
7. (b) Zaugg, H. E. Synthesis 1984, 85, 181.
8. (c) Recent examples Vanier, C.; Wagner, A.; Mioskowski, C. Chem. Eur. J. 2001, 7, 2318.
9. (d) Zhang, J.; Wei, C.; Li, C. J. Tetrahedron Lett. 2002, 43, 5731.
10. (e) Schierle-Arndt, K.; Kolter, D.; Danielmeier, K.; Steckhan, E. Eur. J. Org. Chem. 2001, 2425.
11. (f) Okitsu, O.; Suzuki, R.; Kobayashi, S. J. Org. Chem. 2001, 66, 809.
12. (g) Metais, E.; Overman, L. E.; Rodrigues, M. I.; Stearns, B. A. J. Org. Chem. 1997, 62, 9210.
13. (h) Sun, P.; Sun, C.; Weinreb, S. M. J. Org. Chem. 2002, 67, 4337.
14. (i): Veerman, J. N.; Klein, J.; Aben, R. W. M.; Scheeren, H. W.; Kruse, C. G.; van Maarseveen, J. H.; Rutjes, F. P. J. T.; Hiemstra, H. Eur. J. Org. Chem. 2002, 3133. Intramolecular [4 + 2] reaction using N-acyliminium ion:
15. (j) Shimizu, T.; Tanino, K.; Kuwajima, I. Tetrahedron Lett. 2000, 41, 5715.
16. (a) Yoshida, J.; Suga, S.; Suzuki, S.; Kinomura, N.; Yamamoto, A.; Fujiwara, K. J. Am. Chem. Soc. 1999, 121, 9546.
17. (b) Suga, S.; Suzuki, S.; Yamamoto, A.; Yoshida, J. J. Am. Chem. Soc. 2000, 122, 10244.
18. (c) Suga, S.; Okajima, M.; Yoshida, J. Tetrahedron Lett. 2001, 42, 2173.
19. (d) Suga, S.; Suzuki, S.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 30.
20. (e) Yoshida, J.; Suga, S. Chem. Eur. J. 2002, 8, 2650.
21. Although electrochemical and chemical oxidations are widely utilized, N-acyliminium ions thus generated are usually trapped in situ with nucleophiles. For example: (a) Shono, T. Tetrahedron 1984, 40, 811.
22. (b) Moeller, K. D. Tetrahedron 2000, 56, 9527.
23. (c) Naota, T.; Nakato, T.; Murahasi, S. Tetrahedron Lett. 1990, 31, 7475.
24. Suga, S.; Okajima, M.; Fujiwara, K.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 7941.
25. Calculations were carried out at the B3LYP/6-31G(d) level using G98W.
26. (a) Kupfer, R.; Würthwein, E.-U.; Nagle, M.; Allmann, R. Chem. Ber. 1985, 118, 643.
27. (b) Lamatsch, B.; Seebach, D.; Ha, T.-K. Helv. Chim. Acta 1992, 75, 1095.
28. For selective oxidative cleavage of the trimethylsilyl group on the carbon alpha to the nitrogen of carbamates to generate N-acyliminium cation, see: (a) Yoshida, J.; Isoe, S. Tetrahedron Lett. 1987, 28, 6621.
29. (b) Suga, S.; Watanabe, M.; Yoshida, J. J. Am. Chem. Soc. 2002, 124, 14824.
30. Brocherieux-Lanoy, S.; Dhimane, H.; Poupon, J.-C.; Vanucci, C.; Lhommet, G. J. Chem. Soc., Perkin Trans. 1 1997, 2163.
31. Efficient mixing using a micromixer: (a) Ehrfeld, W.; Golbig, K.; Hessel, V.; Löwe, H.; Richter, T. Ind. Eng. Chem. Res. 1999, 38, 1075.
32. (b) Kakuta, M.; Bessoth, F. G.; Manz, A. Chem. Rec. 2001, 1, 395.
33. (c) Stroock, A. D.; Dertinger, S. K. W.; Ajdari, A.; Mezić, I.; Stone, H. A.; Whitesides, G. M. Science 2002, 295, 647.
34. (d) Suga, S.; Nagaki, A.; Yoshida, J. Chem. Commun. 2003, 354.