Pummerer-type α-functionalization of arylseleninylacetates by treating with trimethylsilyl- or tri-n-butylstannyl-masked nucleophiles and trifluoroacetic anhydride or a Lewis acid

Tetrahedron Letters

Volumn 41, Issue 23, 2000, Pages 4637-4640

  Shimada, Kazuaki ^a   Kikuta, Yutaka ^a   Koganebuchi, Hiroyuki ^a   Yonezawa, Fumi ^a   Aoyagi, Shigenobu ^a   Takikawa, Yuji ^a  

^a IWATE UNIVERSITY   (Japan)

Author keywords

Allyltrimethylsilane; Pummerer rearrangement; Selenoxide; azidation; allylation

Indexed keywords

SELENIDE; SILANE DERIVATIVE; TIN DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; REACTION ANALYSIS;

EID: 0034640963     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00681-X     Document Type: Article

References (35)

1. (a) Renard, M.; Hevesi, L. Tetrahedron Lett. 1983, 24, 3911-3912.
2. (b) Silveira, C. C.; Comasseto, J. V.; Catani, V. Synth. Commun. 1985, 15, 931-937.
3. (c) Hevesi, L. Phosphorus and Sulfur 1988, 38, 191-200.
4. (d) Hevesi, L.; Lavoix, A. Tetrahedron Lett. 1989, 30, 4433-4434.
5. (e) Hermans, B.; Hevesi, L. Tetrahedron Lett. 1990, 31, 4363-4366.
6. (f) Hevesi, L. Bull. Soc. Chim. Fr. 1990, 127, 697-703.
7. (g) Silveira, C. C.; Lenardão, E. J.; Comasseto, J. V.; Dabdoub, M. J. Tetrahedron Lett. 1991, 32, 5741-5744.
8. (h) Hevesi, L. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67, 155-168.
9. (i) Silveira, C. C.; Araujo, M. A.; Lenardão, E. J.; Braga, A. L.; Dabdoub, M. J. Synthesis 1995, 1305-1310.
10. (j) Hermans, B.; Hevesi, L. J. Org. Chem. 1995, 60, 6141-6147.
11. Surowiec, K.; Fuchigami, T. J. Org. Chem. 1992, 57, 5781-5783.
12. (a) Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1973, 95, 2697-2699.
13. (b) Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434-5447.
14. (c) Reich, H. J. Acc. Chem. Res. 1979, 12, 22-30 and references cited therein.
15. (d) Davis, F. A.; Billmers, J. M.; Stringer, O. D. Tetrahedron Lett. 1983, 24, 3191-3194.
16. (e) Kamigata, N. Yuki Gosei Kagaku Kyokaishi 1990, 48, 229-239 and references cited therein.
17. (f) Reich, H. J.; Yelm, K. E. J. Org. Chem. 1991, 56, 5672-5679.
18. (g) Kamigata, N.; Shimizu, T. Reviews on Heteroatom Chemistry 1991, 4, 226-248 and references cited therein.
19. (h) Davis, F. A.; Reddy, R. T. J. Org. Chem. 1992, 57, 2599-2606.
20. (i) Takahashi, T.; Kurose, N.; Kawanami, S.; Arai, Y.; Koizumi, T.; Shiro, M. J. Org. Chem. 1994, 59, 3262-3264.
21. (j) Bosch, E.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 1 1996, 2731-2738.
22. (k) Stuhr-Hansen, N.; Sørensen, H. O.; Henriksen, L.; Larsen, S. Acta Chem. Scand. 1997, 51, 1186-1191.
23. (l) Shimizu, T.; Enomoto, M.; Taka, H.; Kamigata, N. J. Org. Chem. 1999, 64, 8242-8247.
24. (a) Sonoda, N.; Miyoshi, N. Tetrahedron Lett. 1977, 851-854.
25. (b) Fujihara, H.; Saito, R.; Yabe, M.; Furukawa, N. Chem. Lett. 1992, 1437-1440.
26. (c) Uneyama, K.; Tokunaga, Y.; Maeda, K. Tetrahedron Lett. 1993, 34, 1311-1312.
27. (d) Löwe, W.; Rütjes, T. J. Heterocycl. Chem. 1995, 32, 43-48.
28. Physical data of compounds 1-16 are available as the supplementary materials.
29. (a) Horn, V.; Paetzold, R. Z. Anorg. Allg. Chem. 1973, 398, 186-192.
30. (b) Marino, J. P.; Larsen Jr., R. D. J. Am. Chem. Soc. 1981, 103, 4642-4643.
31. (c) Uemura, S.; Fukuzawa, S. J. Chem. Soc., Perkin Trans. 1 1985, 471-480.
32. (d) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Bartoli, D. Gazz. Chim. Ital. 1987, 117, 423-427.
33. (e) Kurose, N.; Takahashi, T.; Koizumi, T. Tetrahedron 1997, 53, 12115-12129.
34. (f) Takahashi, T.; Nakano, N.; Koizumi, T. Tetrahedron: Asymmetry 1997, 8, 3293-3308.
35. (g) Zhang, J.; Kurose, N.; Saito, S.; Takahashi, T.; Koizumi, T. Yuki Gosei Kagaku Kyokaishi 1999, 57, 587-597 and references cited therein.