Stereoselective synthesis of substituted dienes by the double ortho ester Claisen rearrangement

Tetrahedron Letters

Volumn 46, Issue 5, 2005, Pages 779-782

  Hong, Suk Pyo ^a   Yoon, Sung Jun ^a   Yu, Byung Chan ^a  

^a Mokwon University   (South Korea)

Author keywords

(E) 1,3 dienes; Diels Alder cycloaddition; Substituted propargylic diols; The double ortho ester Claisen rearrangement

Indexed keywords

ALKADIENE; ESTER DERIVATIVE;

ARTICLE; CLAISEN REARRANGEMENT; CYCLOADDITION; DIELS ALDER REACTION; QUANTUM YIELD; REPRODUCIBILITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

BETULACEAE;

EID: 11844265911     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.015     Document Type: Article

References (16)

1. W.S. Johnson, L. Werthmann, W.R. Bartlett, T.J. Brockson, T.T. Li, D.J. Faulkner, and M.R. Peterson J. Am. Chem. Soc. 92 1970 741
2. For review articles on the Claisen rearrangement: F.E. Ziegler Chem. Rev. 88 1988 1423
3. R. Lutz Chem. Rev. 84 1984 206
4. F.E. Ziegler Acc. Chem. Res. 10 1977 227
5. G.B. Bennett Synthesis 1977 589
6. G. Stork, and S. Raucher J. Am. Chem. Soc. 98 1976 1583
7. G.W. Daub, J.P. Edwards, C.R. Okada, J.W. Allen, C.T. Maxey, M.S. Wells, A.S. Goldstein, M.J. Dibley, C.J. Wang, D.P. Ostercamp, S. Chung, P.S. Cunningham, and M.A. Berliner J. Org. Chem. 62 1997 1976 and references therein
8. M.A. Handerson, and C.H. Heathcock J. Org. Chem. 53 1988 4736
9. J.D. Ha, and J.K. Cha J. Am. Chem. Soc. 121 1999 10012
10. M. Bertrand, and J. Viala Tetrahedron Lett. 19 1978 2575
11. E. Egert, D. Schumidt, C. Gonschorreck, and D. Hoppe Tetrahedron Lett. 28 1987 789
12. U. Behrens, D. Wolff, and D. Hoppe Synthesis 1991 644
13. Y. Ishino, I. Nishiguchi, K. Kim, and T. Hirashima Synthesis 1982 740
14. The diols 3, 7 and 17 were prepared by the following steps:
15. For other examples of the endo Diels-Alder adducts using maleic anhydride as dienophile, see: G. Helmchen Stereoselective Synthesis Vol. 5 1996 Georg Thieme Stuttgart: New York 2802
16. +, 12), 361 (25), 333 (100), 304 (6), 287 (55), 277 (11), 259 (87), 221 (7), 205 (65), 177 (71), 165 (25), 149 (30), 132 (18), 121 (22), 105 (93), 93 (17), 83 (40), 67 (13)