Unexpected epimerization and stereochemistry revision of IMDA adducts from sorbate-related 1,3,8-nonatrienes

Tetrahedron Letters

Volumn 48, Issue 37, 2007, Pages 6543-6547

  Wu, Jinlong ^a   Yu, Haihua ^a   Wang, Yan ^a   Xing, Xinglong ^b   Dai, Wei Min ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Intramolecular Diels Alder reaction; Isomerization; Lactone; Microwave; Sorbate; Stereochemistry

Indexed keywords

SORBIC ACID; TRIENTINE;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLOADDITION; DIELS ALDER REACTION; EPIMERIZATION; HIGH TEMPERATURE; ISOMERIZATION; MICROWAVE RADIATION; PURIFICATION; REACTION ANALYSIS; SEPARATION TECHNIQUE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

ALNUS;

EID: 34547757007     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.046     Document Type: Article

References (36)

1. Taber D.F. Intramolecular Diels-Alder and Alder Ene Reactions (1984), Springer, Berlin
2. Fallis A.G. Can. J. Chem. 62 (1984) 183-234
3. Ciganek E. Org. React. 32 (1984) 1-374
4. Craig D. Chem. Soc. Rev. (1987) 187-238
5. Roush W.R. In: Curran D.P. (Ed). Advances in Cycloaddition Vol. 2 (1990), JAI, Greenwich, CT 91-146
6. Roush W.R. In: Trost B.M., Fleming I., and Paquette L.A. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford 513-550
7. Craig D. In: Helmchen G., Hoffmann R.W., Mulzer J., and Schumann E. (Eds). Stereoselective Synthesis. 4th ed. Methods of Organic Chemistry (Houben-Weyl) Vol. E21c (1995), Thieme, Stuttgart 2872-2904
8. Bear B., Sparks S.M., and Shea K.J. Angew. Chem., Int. Ed. 40 (2001) 820-849
9. Stocking E.M., and Williams R.M. Angew. Chem., Int. Ed. 42 (2003) 3078-3115
10. For IMDA reactions of sorbate esters, see:. Boeckman Jr. R.K., and Demko D.M. J. Org. Chem. 47 (1982) 1789-1792
11. Martin S.F., Williamson S.A., Gist R.P., and Smith K.M. J. Org. Chem. 48 (1983) 5170-5180
12. Cayzer T.N., Paddon-Row M.N., Moran D., Payne A.D., Sherburn M.S., and Turer P. J. Org. Chem. 70 (2005) 5561-5570
13. Paddon-Row M.N., Moran D., Jones G.A., and Sherburn M.S. J. Org. Chem. 70 (2005) 10841-10853 and references cited therein
14. Wu J., Sun L., and Dai W.-M. Tetrahedron 62 (2006) 8360-8372 and references cited therein
15. Brown F.K., and Houk K.N. Tetrahedron Lett. 26 (1985) 2297-2300
16. Raimondi L., Brown F.K., Gonzalez J., and Houk K.N. J. Am. Chem. Soc. 114 (1992) 4796-4804
17. For microwave-assisted Wittig reaction, see:. Wu J., Wu H., Wei S., and Dai W.-M. Tetrahedron Lett. 45 (2004) 4401-4404
18. Wu J., Li D., Wu H., Sun L., and Dai W.-M. Tetrahedron 62 (2006) 4643-4650
19. For microwave-assisted heterocycle synthesis, see:. Dai W.-M., Wang X., and Ma C. Tetrahedron 61 (2005) 6879-6885
20. Feng G., Wu J., and Dai W.-M. Tetrahedron 62 (2006) 4635-4642
21. Xing X., Wu J., Feng G., and Dai W.-M. Tetrahedron 62 (2006) 6774-6781
22. Xing X., Wu J., Luo J., and Dai W.-M. Synlett (2006) 2099-2103
23. Xing X., Wu J., and Dai W.-M. Tetrahedron 62 (2006) 11200-11206
24. Feng G., Wu J., and Dai W.-M. Tetrahedron Lett. 48 (2007) 401-404
25. For microwave-assisted solid-phase indole synthesis, see:. Dai W.-M., Guo D.-S., Sun L.-P., and Huang X.-H. Org. Lett. 5 (2003) 2919-2922
26. Sun L.-P., and Dai W.-M. Angew. Chem., Int. Ed. 45 (2006) 7255-7258
27. For recent reviews on controlled microwave heating, see:. Nüchter M., Ondruschka B., Bonrath W., and Gum A. Green Chem. 43 (2004) 128-141
28. Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284
29. For recent monographs, see:. Kappe C.O., and Stadler A. Microwaves in Organic and Medicinal Chemistry (2005), Wiley-VCH, Weinheim
30. In: Loupy A. (Ed). Microwaves in Organic Synthesis Vols. 1 and 2 (2006), Whiley-VCH, Weinheim
31. 4
32. +), 247.0941; found, 247.0936.
33. 4: C, 64.27; H, 7.19. Found: C, 64.22; H, 7.19.
34. The crystallographic data (excluding structure factors) of 11, 12, and 14 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 648332, CCDC 648333, and CCDC 648334, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44-(0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
35. 4: C, 71.31; H, 6.34. Found: C, 71.29; H, 6.34.
36. 4: C, 71.31; H, 6.34. Found: C, 71.31; H, 6.33.