A facile method for the stereoselective preparation of (1Z,3E)-dienyl ethers via 1,4-elimination of 1,4-dialkoxy-(2Z)-alkenes with n-butyllithium

Synlett

Volumn , Issue 6, 2006, Pages 849-852

  Tayama, Eiji ^a   Sugai, Sayaka ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

1,4 eliminations; Dienyl acetals; Dienyl ethers; Precoordinations; Stereo selective synthesis

Indexed keywords

1 ALKOXY 4 METHOXY ALKENE DERIVATIVE; 1 SILOXY 4 METHOXY ALKENE DERIVATIVE; ALKENE DERIVATIVE; BUTYLLITHIUM; ETHER; ETHER DERIVATIVE; LITHIUM DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ELIMINATION REACTION; STEREOCHEMISTRY;

EID: 33645766566     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939053     Document Type: Article

References (35)

1. For reviews, see: (a) Tomooka, K. In The Chemistry of Organolithium Compounds, Vol. 2; Rappoport, Z.; Marek, I., Eds.; John Wiley and Sons Ltd.: Chichester, 2004, 749-828.
2. (b) Clayden, J. In Organolithiums: Selectivity for Synthesis; Baldwin, J. E.; Williams, R. M., Eds.; Pergamon: Manchester, 2002, Chap. 8.
3. (c) Tomooka, K.; Yamamoto, H.; Nakai, T. Liebigs Ann./Recl. 1997, 1275.
4. (d) Nakai, T.; Mikami, K. Org. React. 1994, 46, 105.
5. (e) Brückner, R. In Comprehensive Organic Synthesis, Vol. 6; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991, Chap. 4.6.
6. (a) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
7. (b) Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161.
8. (a) Inui, M.; Hosokawa, S.; Nakazaki, A.; Kobayashi, S. Tetrahedron Lett. 2005, 46, 3245.
9. (b) Suzuki, T.; Inui, M.; Hosokawa, S.; Kobayashi, S. Tetrahedron Lett. 2003, 44, 3713.
10. Danishefsky, S.; Kitahara, T. J. Am. Chem. Soc. 1974, 96, 7807.
11. For a review of 1,3-dienyl silyl ethers (silyl dienol ethers), see: Brownbridge, P. Synthesis 1983, 85.
12. Previous preparation of 1,3-dienyl silyl ethers: (a) Choi, J.; Imai, E.; Mihara, M.; Oderaotoshi, Y.; Minakata, S.; Komatsu, M. J. Org. Chem. 2003, 68, 6164.
13. (b) Janey, J. M.; Iwama, T.; Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 2000, 65, 9059.
14. (c) Moreno, M. J. S. M.; Martins, R. M. L. M.; Melo, M. L. S.; Neves, A. S. C. Chem. Lett. 1997, 529.
15. Tominaga, Y.; Kamio, C.; Hosomi, A. Chem. Lett. 1989, 1761.
16. (e) Iqbal, J.; Khan, M. A. Synth. Commun. 1989, 19, 515.
17. (f) Cazeau, P.; Duboudin, F.; Moulines, F.; Babot, O.; Dunogues, J. Tetrahedron 1987, 43, 2089.
18. (g) Colvin, E. W.; Thom, I. G. Tetrahedron 1986, 42, 3137.
19. (h) Casey, C. P.; Jones, C. R.; Tukada, H. J. Org. Chem. 1981, 46, 2089.
20. (i) Hirai, K.; Suzuki, H.; Morooka, Y.; Ikawa, T. Tetrahedron Lett. 1980, 21, 3413.
21. (j) Miller, R. D.; McKean, D. R. Synthesis 1979, 730.
22. (k) House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324.
23. Previous preparation of alkyl 1,3-dienyl ethers: (a) Gilbert, J. C.; Weerasooriya, U. J. Org. Chem. 1983, 48, 448.
24. (b) Hiranuma, H.; Miller, S. I. J. Org. Chem. 1982, 47, 5083.
25. (c) Dowd, P.; Weber, W. J. Org. Chem. 1982, 47, 4774.
26. (d) Kluge, A. F.; Cloudsdale, I. S. J. Org. Chem. 1979, 44, 4847.
27. (e) Earnshaw, C.; Wallis, C. J.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1979, 3099.
28. A similar type of 1,4-elimination reaction has been reported using alkenyl acetals: Canepa, C.; Prandi, C.; Sacchi, L.; Venturello, P. J. Chem. Soc., Perkin Trans. 1 1993, 1875.
29. 2 (1 atm), 5% Lindlar cat., quinoline, MeOH, r.t.
30. 2OP via the literature procedure (ref. 7d).
31. 2C≡CH according to the same three-step procedure as described for 1b (ref. 9).
32. 2O without substrates.
33. The complete 1Z-to-1E changeover was observed in the case of 1d. The reaction of silyl derivative 1b in THF under the same conditions gave a mixture of stereoisomers without any detectable retro-Brook rearrangement product: (1Z,3E)/(1Z,3Z)/(1E,3E)/(1E,3Z) = 42:1:16:21 (yield, %).
34. 2O instead of THF gave almost the same results.
35. Hartung, J.; Kneuer, R. Eur. J. Org. Chem. 2000, 1677.