A Vinylogous Donor in an Iron(III)-Catalysed Michael Reaction and an Enone-Dienol Tautomerism

European Journal of Organic Chemistry

Volumn , Issue 5, 1998, Pages 759-761

  Christoffers, Jens ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Carbonyl compounds; Catalysis; Iron compounds; Michael reactions; Tautomerism

Indexed keywords

EID: 0002270993     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199805)1998:5<759::AID-EJOC759>3.0.CO;2-W     Document Type: Article

References (16)

1. E. D. Bergmann, D. Ginsburg, R. Pappo, Org. React. 1959, 10, 179-555.
2. [2a] R. L. Funk, J. F. Fitzgerald, T. A. Olmstead, K. S. Para, J. A. Wos, J. Am. Chem. Soc. 1993, 115, 8849-8850.
3. [2b] M. Kato, V. P. Kamat, A. Yoshikoshi, Synthesis 1988, 699-701.
4. [2c] H. J. Reich, J. M. Renga, I. L. Reich, J. Am. Chem. Soc. 1974, 97, 5434-5447.
5. A G. Schultz, M. A. Holoboski, Tetrahedron Lett. 1993. 34, 3021-3024.
6. [4a] A. Bernadi, K. Karamfilova, S. Sanguinetti, C. Scolastico, Tetrahedron 1997, 53, 13009-13026.
7. [4b] R. A. Bunce, M. F. Schlecht, W. G. Dauben, C. H. Heathcock, Tetrahedron Lett. 1983, 24, 4943-4946.
8. [4c] J. N. Marx, G. Minaskanian, J. Org. Chem. 1982, 47, 3306-3310.
9. [5a] J. Christoffers, J. Chem. Soc., Chem. Commun. 1997, 943-944.
10. [5b] J. Christoffers, J. Chem. Soc., Perkin Trans. 1 1997, 3141-3149.
11. [6a] J.-F. Lavallee, C. Spino, R. Ruel, K. T. Hogan, P. Deslongchamps, Can. J. Chem. 1992, 70, 1406-1426.
12. [6b] J. Bruhn, H. Heimgartner, H. Schmidt, Helv. Chim. Acta 1979, 62, 2630-2654.
13. In compound 3, which was obtained as a single diastereomer, the relative configuration of C-8 could not be determined, not even when applying 2D/NOE experiments.
14. It is surprising that this is the first report on this equilibrium, although systems like 1 have been intensively studied in the literature.
15. The equilibrium is somewhat dependent from the solvent and additives, but always in the range of about 1:1.
16. f = 0.65 (4)].