"Syn effect" in the 1,4-eliminative ring opening of [3-substituted (E)-1-propenyl]oxiranes to the corresponding 2,4-dienyl alcohols

Chemistry Letters

Volumn 34, Issue 8, 2005, Pages 1140-1141

  Takeda, Naohiro ^a   Chayama, Takuya ^a   Takenaka, Hiroyuki ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 26844514850     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.1140     Document Type: Article

References (27)

1. A. Shibayama, T. Nakamura, T. Asada, T. Shintani, Y. Ukaji, H. Kinoshita, and K. Inomata, Bull. Chem. Soc. Jpn., 70, 381 (1997).
2. The "syn-effect" is herein defined as an effect which stabilizes the syn-conformation against the steric hindrance.
3. Related studies on the "syn-effect": a) T. Hirata, Y. Sasada, T. Ohtani, T. Asada, H. Kinoshita, H. Senda, and K. Inomata, Bull. Chem. Soc. Jpn., 65, 75 (1992).
4. b) T. Nakamura, S. K. Guha, Y. Ohta, D. Abe, Y. Ukaji, and K. Inomata, Bull. Chem. Soc. Jpn., 75, 2031 (2002).
5. c) S. K. Guha, A. Shibayama, D. Abe, Y. Ukaji, and K. Inomata, Chem. Lett., 32, 778 (2003).
6. d) S. K. Guha, Y. Ukaji, and K. Inomata, Chem. Lett., 32, 1158 (2003).
7. e) S. K. Guha, A. Shibayama, D. Abe, M. Sakaguchi, Y. Ukaji, and K. Inomata, Bull. Chem. Soc. Jpn., 77, 2147 (2004). See also references cited therein.
8. H. Takenaka, Y. Ukaji, and K. Inomata, Chem. Lett., 34, 256 (2005).
9. R. P. Thummel and B. Rickborn, J. Org. Chem., 37, 4250 (1972);
10. J. R. Falck, S. Manna, J. Capdevila, and J. D. Buynak, Tetrahedron Lett., 24, 5719 (1983);
11. E. J. Corey, M. M. Mehrotra, and W. Su, Tetrahedron Lett., 26, 1919 (1985);
12. J. S. Yadav, D. K. Barma, and D. Dutta, Tetrahedron Lett., 38, 4479 (1997);
13. D. Lançois and J. Maddaluno, Tetrahedron Lett., 39, 2335 (1998).
14. When [3-alkyl-substituted (E)-1-propenyl]oxiranes without spiro cyclohexane ring were subjected to the 1,4-eliminative ring opening instead of vinyloxiranes 1, the desired rearranged products were not obtained, but a mixture of by-products were formed presumably via ring-opening alkylation of oxiranes: D. M. Hodgson, M. J. Fleming, and S. J. Stanway, J. Am. Chem. Soc., 126, 12250 (2004).
15. δ bond was discussed.
16. β bond was E might be formed via conformation E. (Chemical Equation Presented)
17. a) T. Laube and H. U. Stilz, J. Am. Chem. Soc., 109, 5876 (1987).
18. b) T. Laube and T.-K. Ha, J. Am. Chem. Soc., 110, 5511 (1988).
19. c) P. R. Rablen, R. W. Hoffmann, D. A. Hrovat, and W. T. Borden, J. Chem. Soc., Perkin Trans. 2, 1999, 1719.
20. Y. Apeloig, P. v. R. Schleyer, and J. A. Pople, J. Am. Chem. Soc., 99, 5901 (1977).
21. P. v. R. Schleyer, J. D. Dill, J. A. Pople, and W. J. Hehre, Tetrahedron, 33, 2497 (1977);
22. D. Cremer, J. Am. Chem. Soc., 101, 7199 (1979);
23. K. N. Houk, R. W. Strozier, N. G. Rondan, R. R. Fraser, and N. Chuaqui-Offermanns, J. Am. Chem. Soc., 102, 1426 (1980).
24. U. Schöllkoph, Angew. Chem., Int. Ed., 9, 763 (1970);
25. J. A. Marshall, "Comprehensive Organic Synthesis," ed. by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 3, pp 979-981;
26. K. Tomooka, J. Synth. Org. Chem. Jpn., 59, 322 (2001).
27. V. Rautenstrauch, G. Büchi, and H. Wüest, J. Am. Chem. Soc., 96, 2576 (1974).