Palladium(II)-catalyzed asymmetric 1,4-oxidation of 2-phenyl-1,3-cyclohexadiene

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8541-8544

  Thorarensen, Atli ^a   Palmgren, Andreas ^a   Itami, Kenichiro ^a   Bäckvall, Jan E ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; OXIDATION; STEREOCHEMISTRY;

EID: 0030669110     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10242-8     Document Type: Article

References (22)

1. (a) Bäckvall, J. E. "Palladium-Catalyzed 1,4-Additions to Conjugated Dienes", review in Metal-catalyzed Cross Coupling Reactions, Eds. P. Stang and F. Diederich, Wiley-VCH, Weinham, in press.
2. (b) Bäckvall, J. E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
3. (c) Tsuji, J. "Palladium Reagents and Catalysts: Innovations in Organic Synthesis" Wiley, Chichester, 1995.
4. (d) Harrington, P. J. "Transitiom Metal Allyl Complexes: Pd, W, Mo-assisted Nucleophilic Attack" in Comprehensive Organometallic Chemistry II, Eds. Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Pergamon, Oxford, 1995, vol. 12 (vol. Ed. Hegedus, L. S.), pp 797-904.
5. (a) Bäckvall, J. E.; Tanner, D. "Palladium-mediated synthesis of alkaloids", in Studies in Natural Products Chemistry, Atta-ur-Rahman, Elsevier, Amsterdam, 1995, vol. 16, pp 415-452.
6. (b) Andersson, P. G.; Bäckvall, J. E. "Synthesis of heterocyclic natural products via regio- and stereocontrolled palladium-catalyzed reactions", in Advances in Heterocyclic Natural Product Synthesis, Ed. Pearson, W. H., JAI Press, Greenwich, CT, 1996, vol. 3, pp 179-215.
7. Trost, B. M.; Van Vranken, D. L.; Chem. Rev. 1996, 96, 395.
8. (a) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063.
9. (b) Hosokawa, T.; Uno, T.; Inui, S.; Murahashi, S. I. J. Am. Chem. Soc. 1981, 103, 2318.
10. (c) Hosokawa, T.; Okuda, C.; Murahashi, S. I. J. Org. Chem. 1985, 50, 1282.
11. Bäckvall, J. E.; Nordberg, R. E.; Wilhelm, D. J. Am. Chem. Soc. 1985, 107, 6892.
12. (a) Nilsson, Y. M.; Aranyos, A.; Andersson, P. G.; Bäckvall, J. E.; Parrain, J. L.; Ploteau, C.; Quintard, J. P. J. Org. Chem. 1996, 61, 1825.
13. (b) Thorarensen, A.; Palmgren, A.; Bäckvall, J. E. unpublished results.
14. (c) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779.
15. Sulfoxide 4 has been demonstrated to accelerate the 1,4-oxidation of dienes: Grennberg, H.; Gogoll, A.; Bäckvall, J. E. J. Org. Chem. 1991, 56, 5808.
16. The detailed synthesis of the ligands will be reported in due course. Ligand 4 was prepared from 5-bromo-2-t-butyl-1,4-dimetoxybenzene; Ahmad, F. B. H. Chem. Abstr. 1989, 110, 23454e. The 2,5-dicarbonyl ligands were prepared in five steps from 2,4-dihydroxy-1,4-benzene dicarboxylic acid ethyl ester: Reinhart, B. A.; Unroe, M. R. Chem. Abstr. 1990, 112, 157874s.
17. The detailed synthesis of the ligands will be reported in due course. Ligand 4 was prepared from 5-bromo-2-t-butyl-1,4-dimetoxybenzene; Ahmad, F. B. H. Chem. Abstr. 1989, 110, 23454e. The 2,5-dicarbonyl ligands were prepared in five steps from 2,4-dihydroxy-1,4-benzene dicarboxylic acid ethyl ester: Reinhart, B. A.; Unroe, M. R. Chem. Abstr. 1990, 112, 157874s.
18. The absolute configuration of the major enantiomer of trans-2 has not been determined.
19. Diene1 was prepared by two different procedures: (a) Reich, H. J.; Wollowitz, S. J. Am. Chem. Soc. 1982, 104, 7051.
20. (b) Karlström, A. S. E.; Rönn, M.; Thorarensen, A.; Bäckvall, J. E. submitted for publication.
21. (c) Rönn, M. 'Studies on Palladium(II)-Catalyzed Aerobic Oxidations of Olefins and Conjugated Dienes in DMSO' in 'Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology' 274, 1997.
22. Other reaction parameters such as solvents and other additives were found to affect the reaction, though not as dramatically.