The sequential ester dienolate [2,3]-Wittig/3-oxy-cope rearrangement. New access to substituted α-keto esters

Synlett

Volumn , Issue 3, 2000, Pages 415-417

  Hiersemann, Martin ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

keto esters; Dienolates; Domino reactions; Pericyclic reactions; Rearrangements

Indexed keywords

ALKENE DERIVATIVE; ESTER DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0034050613     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (15)

1. Hiersemann, M. Synlett 1999, 1823.
2. Mikami, T.; Kishi, N.; Nakai, T.; Fujita, Y. Tetrahedron 1986, 42, 2911.
3. For the synthesis of 3-hydroxy-1,5-hexadienes via the [2,3]-Wittig rearrangement of allylic ethers and the subsequent oxyCope rearrangement, see Tomooka, K.; Wei, S.; Nakai, T. Chem. Lett. 1991, 43, and references cited therein.
4. Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron Lett. 1983, 24, 1157.
5. For the domino [2,3]-Wittig I oxy-Cope rearrangement of bisallylic ethers, see Greeves, N.; Lee, W. Tetrahedron Lett. 1997, 58, 6445.
6. For reviews concerning domino reactions, see a) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 32, 131.
7. b) Tietze, L. F. Chem. Rev. 1996, 96, 115.
8. a) Hiersemann, M. Tetrahedron 1999, 55, 2625.
9. b) Hiersemann, M.; Lauterbach, C. Pollex, A. Eur. J. Org. Chem. 1999, 2713.
10. 3 (288.4): calcd. C 74.97, H 8.39; found C 75.35, H 8.58.
11. For the influence of substituent effects on the mechanism of the Cope rearrangement, see a) W. v. E. Doering, Y. Wang J. Am. Chem. Soc. 1999, 121, 10112
12. b) D. A. Hrovat, B. R. Reno, H. Lange, H. Yoo, K. N. Houk, W. Thatcher Borden J. Am. Chem. Soc. 1999, 121, 10529.
13. 3 (226.3): calcd. C 68.99, H 9.15; found C 69.20, H 9.97.
14. For the oxy-Cope rearrangement of a 3-(N,N-diethylamino)carbonyl-3-hydroxy-substituted 1,5-hexadiene, see Koft, E. R.; Williams, M. D. Tetrahedron Lett. 1986, 27, 2227.
15. For the thermal and the Lewis acid catalyzed type II intramolecular carbonyl ene reaction of a δ,ε-unsaturated aldehyde, see Johnston, M. I.; Kwass, J. A. Beal, R. B., Snider, B. B. J. Org. Chem. 1987, 52, 5419.