[2,3]-Wittig sigmatropic rearrangement of γ-allyloxy-β-enaminoesters

Synlett

Volumn , Issue 5, 2003, Pages 663-666

  Pévet, Isabelle ^a   Meyer, Christophe ^a   Cossy, Janine ^a  

^a CNRS   (France)

Author keywords

Lactones; Lithiation; Wittig rearrangement; enaminoesters; ketoesters

Indexed keywords

5 ALLYL 4 (BENZYLAMINO)FURAN 2(5H) ONE; ALLYL COMPOUND; ESTER; ETHYL 4 (ALLYLOXY) 3 (BENZYLAMINO)BUT 2 ENOATE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGEN BOND; METHODOLOGY; POLYMERIZATION; ROOM TEMPERATURE; SYNTHESIS; WITTIG REARRANGEMENT;

EID: 0037270110     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38362     Document Type: Article

References (51)

1. (a) Effenberger, F.; Syed, J. Tetrahedron: Asymmetry 1998, 9, 817.
2. (b) Bühler, H.; Bayer, A.; Effenberger, F. Chem.-Eur. J. 2000, 6, 2564; and references cited therein.
3. (a) Hiyama, T.; Oishi, H.; Saimoto, H. Tetrahedron Lett. 1985, 26, 2459.
4. (b) Hiyama, T.; Oishi, H.; Suetsugu, Y.; Nishide, K.; Saimoto, H. Bull. Chem. Soc. Jpn. 1987, 60, 2139.
5. (c) Syed, J.; Förster, S.; Effenberger, F. Tetrahedron: Asymmetry 1998, 9, 805.
6. (d) Wang, J.; Jiang, X.; Chen, M.; Ge, Z.; Hu, Y.; Hu, H. J. Chem. Soc., Perkin Trans. 1 2001, 66; and references cited in these articles.
7. (a) Greenhill, J. V.; Ramli, M.; Tomassini, T. J. Chem. Soc., Perkin Trans. 1 1975, 588.
8. (b) Boosen, K.-J. Helv. Chim. Acta 1977, 60, 1256.
9. (c) Schmidt, R. R.; Talbiersky, J. Angew. Chem., Int. Ed. Engl. 1978, 17, 204.
10. (d) Momose, T.; Toyooka, N.; Nishi, T.; Takeuchi, Y. Heterocycles 1988, 27, 1907.
11. (e) Martin, M. R.; Mateo, A. I. Tetrahedron: Asymmetry 1994, 5, 1385.
12. (f) Veronese, A. C.; Callegari, R.; Basato, M.; Valle, G. J. Chem. Soc., Perkin Trans. 1 1994, 1779.
13. (a) Nishide, K.; Aramata, A.; Kamanaka, T.; Inoue, T.; Node, M. Tetrahedron 1994, 50, 8337.
14. (b) Schlessinger, R. H.; Iwanowicz, E. J.; Springer, J. P. Tetrahedron Lett. 1988, 29, 1489.
15. (c) Schlessinger, R. H.; Mjalli, A. M. M.; Adams, A. D.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1992, 57, 2992.
16. (d) Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246.
17. (e) Schlessinger, R. H.; Li, Y.-J. J. Am. Chem. Soc. 1996, 118, 3301.
18. (f) Dankwardt, S. M.; Dankwardt, J. W.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4971.
19. (g) Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4979.
20. (a) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613.
21. (b) Cook, G. R.; Behloz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575.
22. (c) Hitotsuyanagi, Y.; Kobayashi, M.; Fukuyo, M.; Takeya, K.; Itokawa, H. Tetrahedron Lett. 1997, 38, 8295.
23. Pévet, I.; Meyer, C.; Cossy, J. Tetrahedron Lett. 2001, 42, 5215.
24. (a) Aberhart, D. J.; Lin, H.-J. J. Org. Chem. 1981, 46, 3749.
25. (b) Shieh, T.-L.; Lin, C.-T.; McKenzie, A. T.; Byrn, S. R. J. Org. Chem. 1983, 48, 3103.
26. (c) Melillo, D. G.; Cvetovich, R. J.; Ryan, K. M.; Sletzinger, M. J. Org. Chem. 1986, 51, 1498.
27. (d) Hiyama, T.; Kobayashi, K.; Nishide, K. Bull. Chem. Soc. Jpn. 1987, 60, 2127.
28. (e) Pawlak, J. M.; Khau, V. V.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1996, 61, 9055.
29. (f) Soloshonok, V. A.; Kukhar, V. P. Tetrahedron 1996, 52, 6953.
30. (g) Cavé, C.; Gassama, A.; Mahuteau, J.; d'Angelo, J.; Riche, C. Tetrahedron Lett. 1997, 38, 4773.
31. 4 is well-documented, the double metalation of primary or secondary ones has not been reported to our knowledge. See: (a) Schlessinger, R. H.; Iwanowicz, E. J.; Springer, J. P. J. Org. Chem. 1986, 51, 3073. (b) Schlessinger, R. H.; Li, Y.-J.; Von Langen, D. J. J. Org. Chem. 1996, 61, 3226. (c) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 37, 1331. (d) Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983. (e) Schlessinger, R. H.; Pettus, L. H. J. Org. Chem. 1998, 63, 9089. (f) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1999, 40, 1257.
32. 4 is well-documented, the double metalation of primary or secondary ones has not been reported to our knowledge. See: (a) Schlessinger, R. H.; Iwanowicz, E. J.; Springer, J. P. J. Org. Chem. 1986, 51, 3073. (b) Schlessinger, R. H.; Li, Y.-J.; Von Langen, D. J. J. Org. Chem. 1996, 61, 3226. (c) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 37, 1331. (d) Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983. (e) Schlessinger, R. H.; Pettus, L. H. J. Org. Chem. 1998, 63, 9089. (f) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1999, 40, 1257.
33. 4 is well-documented, the double metalation of primary or secondary ones has not been reported to our knowledge. See: (a) Schlessinger, R. H.; Iwanowicz, E. J.; Springer, J. P. J. Org. Chem. 1986, 51, 3073. (b) Schlessinger, R. H.; Li, Y.-J.; Von Langen, D. J. J. Org. Chem. 1996, 61, 3226. (c) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 37, 1331. (d) Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983. (e) Schlessinger, R. H.; Pettus, L. H. J. Org. Chem. 1998, 63, 9089. (f) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1999, 40, 1257.
34. 4 is well-documented, the double metalation of primary or secondary ones has not been reported to our knowledge. See: (a) Schlessinger, R. H.; Iwanowicz, E. J.; Springer, J. P. J. Org. Chem. 1986, 51, 3073. (b) Schlessinger, R. H.; Li, Y.-J.; Von Langen, D. J. J. Org. Chem. 1996, 61, 3226. (c) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 37, 1331. (d) Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983. (e) Schlessinger, R. H.; Pettus, L. H. J. Org. Chem. 1998, 63, 9089. (f) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1999, 40, 1257.
35. 4 is well-documented, the double metalation of primary or secondary ones has not been reported to our knowledge. See: (a) Schlessinger, R. H.; Iwanowicz, E. J.; Springer, J. P. J. Org. Chem. 1986, 51, 3073. (b) Schlessinger, R. H.; Li, Y.-J.; Von Langen, D. J. J. Org. Chem. 1996, 61, 3226. (c) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 37, 1331. (d) Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983. (e) Schlessinger, R. H.; Pettus, L. H. J. Org. Chem. 1998, 63, 9089. (f) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1999, 40, 1257.
36. 4 is well-documented, the double metalation of primary or secondary ones has not been reported to our knowledge. See: (a) Schlessinger, R. H.; Iwanowicz, E. J.; Springer, J. P. J. Org. Chem. 1986, 51, 3073. (b) Schlessinger, R. H.; Li, Y.-J.; Von Langen, D. J. J. Org. Chem. 1996, 61, 3226. (c) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 37, 1331. (d) Dankwardt, J. W.; Dankwardt, S. M.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983. (e) Schlessinger, R. H.; Pettus, L. H. J. Org. Chem. 1998, 63, 9089. (f) Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1999, 40, 1257.
37. Due to their moderate stability on silica gel, the β-enamino-esters 5a-c and 8 were conveniently engaged in the rearrangement step without further purification and therefore an excess of n-BuLi (4 equiv) was routinely used in order to ensure an efficient metalation process of these crude compounds at -78°C. The nucleophilic addition of n-BuLl to the ester carbonyl group of lithiated β-enamino-esters, and/or N,O-dilithiated β-enaminoesters arising from the [2,3]-sigmatropic rearrangement, has never been observed as a side reaction. The fact that these species may be considered as vinylogous lithiated carbamates probably accounts for their low reactivity towards n-BuLi.
38. 6
39. 1a
40. General reviews on the [2,3]-Wittig rearrangement: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (b) Marshall, J. A. In Comprehensive Organic Chemistry, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 975-1014. (c) Brückner, R. In Comprehensive Organic Chemistry, Vol. 6; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 873-907. (d) Kallmerten, J. In Houben-Weyl, Methods of Organic Chemistry, Vol. E 21d; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme-Verlag: Stuttgart, 1995, 3757-3809.
41. General reviews on the [2,3]-Wittig rearrangement: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (b) Marshall, J. A. In Comprehensive Organic Chemistry, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 975-1014. (c) Brückner, R. In Comprehensive Organic Chemistry, Vol. 6; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 873-907. (d) Kallmerten, J. In Houben-Weyl, Methods of Organic Chemistry, Vol. E 21d; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme-Verlag: Stuttgart, 1995, 3757-3809.
42. General reviews on the [2,3]-Wittig rearrangement: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (b) Marshall, J. A. In Comprehensive Organic Chemistry, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 975-1014. (c) Brückner, R. In Comprehensive Organic Chemistry, Vol. 6; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 873-907. (d) Kallmerten, J. In Houben-Weyl, Methods of Organic Chemistry, Vol. E 21d; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme-Verlag: Stuttgart, 1995, 3757-3809.
43. General reviews on the [2,3]-Wittig rearrangement: (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885. (b) Marshall, J. A. In Comprehensive Organic Chemistry, Vol. 3; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 975-1014. (c) Brückner, R. In Comprehensive Organic Chemistry, Vol. 6; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, 873-907. (d) Kallmerten, J. In Houben-Weyl, Methods of Organic Chemistry, Vol. E 21d; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme-Verlag: Stuttgart, 1995, 3757-3809.
44. (a) Takahashi O.; Mikami K.; Nakai T. Chem. Lett. 1987, 69.
45. (b) Sudo, A.; Hashimoto, Y.; Kimoto, H.; Hayashi, K.; Saigo, K. Tetrahedron: Asymmetry 1994, 5, 1333.
46. (c) Enders, D.; Backhaus, D. Synlett 1995, 631.
47. (d) Enders, D.; Backhaus, D.; Runsink, J. Tetrahedron 1996, 52, 1503.
48. (e) Enders, D.; Bartsch, M.; Runsink, J. Synthesis 1999, 243.
49. (f) Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. J. J. Tetrahedron Lett. 1997, 38, 2633.
50. (g) Hiersemann, M.; Lauterbach, C.; Pollex, A. Eur. J. Org. Chem. 1999, 2713.
51. (h) Hiersemann, M. Tetrahedron 1999, 55, 2625.