Development of an unusually highly enantioselective hetero-diels - Alder reaction of benzaldehyde with activated dienes catalyzed by hypercoordinating chiral aluminum complexes

Chemistry - A European Journal

Volumn 6, Issue 1, 2000, Pages 123-128

  Simonsen, Klaus B ^a   Svenstrup, Niels ^a   Roberson, Mark ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Aluminum; Asymmetric catalysis; Hetero Diels Alder reactions; Hypercoordination; Reaction mechanisms

Indexed keywords

ALKADIENE; ALUMINUM DERIVATIVE; BENZALDEHYDE; HETEROCYCLIC AMINE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0033982977     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. See for example: a) D. L. Boger, S. N. Weinreb in Hetero Diels-Alder Methodology in Organic Synthesis, Vol. 47 (Ed.: H. H. Wasserman), Academic Press, San Diego, CA, 1987;
2. b) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrian, J. Thorhauge, Acc. Chem. Res. 1999, 32, 605-613;
3. c) L. F. Tietze, G. Kettschau in Stereoselective Hetero-cyclic Synthesis I, Vol. 189 (Ed.: P. Metz), Springer, Berlin, 1997, pp. 1-120;
4. d) H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007-1019;
5. e) M. Petrzilka, J. I. Grayson, Synthesis 1981, 753-786.
6. a) S. J. Danishefsky, M. P. De Ninno, Angew. Chem. 1987, 99, 15-23; Angew. Chem. Int. Ed. Engl. 1987, 26, 15-23;
7. a) S. J. Danishefsky, M. P. De Ninno, Angew. Chem. 1987, 99, 15-23; Angew. Chem. Int. Ed. Engl. 1987, 26, 15-23;
8. b) G. Desimoni, G. Tacconi, Chem. Rev. 1975, 75, 651-692.
9. a) S. J. Danishefsky, E. Larson, D. Askin, N. Kato, J. Am. Chem. Soc. 1985, 107, 1246-1255;
10. b) M. Bednarski, S. J. Danishefsky, J. Am. Chem. Soc. 1986, 108, 7060-7067.
11. G. Qingzhi, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron 1994, 50, 979-988.
12. a) E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910;
13. b) M. T. Mujica, M. M. Alfonso, A. Galindo, J. A. Palenzuela, Tetrahedron 1996, 52, 2167-2176.
14. G. E. Keck, X.-Y. Li, D. Krishamurthy, J. Org. Chem. 1995, 60, 5998-5999.
15. M. Bednarski, C. Maring, S. J. Danishefsky, Tetrahedron Lett. 1983, 24, 3451-3454.
16. S. E. Schaus, J. Brånalt, E. N. Jacobsen, J. Org. Chem. 1998, 63, 403-405.
17. K. Maruoka, T. Itoh, T. Shirasaka, H .Yamamoto, J. Am. Chem. Soc. 1988, 110, 310-312.
18. a) K. B. Simonsen, P. Bayón, R. G. Hazell, K. V. Gothelf, K. A. Jørgensen, J. Am. Chem. Soc. 1999, 121, 3845-3853;
19. b) K. B. Simonsen, K. A. Jørgensen, Q.-S. Hu, L. Pu, Chem. Commun. 1999, 811-812.
20. These catalysts have also been employed for the addition of diethylzinc to aromatic aldehydes, see, for example: Q.-S. Hu, W.-S. Huang, D. Vitharana, X.-F. Zheng, L. Pu, J. Am. Chem. Soc. 1997, 119, 12454-12464.
21. a) K. Maruoka, T. Ooi, Chem. Eur. J. 1999, 5, 829-833;
22. b) T. Ooi, D. Uraguchi, N. Kagoshima, K. Maruoka, J. Am. Chem. Soc. 1998, 120, 5327-5328;
23. c) D. P. Heller, D. R. Goldberg, W. D. Wulff, J. Am. Chem. Soc. 1997, 119, 10551-10552.
24. K. B. Simonsen, K. V. Gothelf, K. A. Jørgensen, J. Org. Chem. 1998, 63, 7536-7538.
25. W.-S. Huang, Q.-S. Hu, L. Pu, J. Org. Chem. 1998, 63, 1364-1365.
26. K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374-4376.
27. Y. Sonoda, K. Kaeriyama, Bull. Chem. Soc. Jpn. 1992, 65, 853-857.
28. M. Rehahn, A. D. Schlüter, W. J. Feast, Synthesis 1988, 386-388.
29. P. J. Cox, W. Wang, V. Snieckus, Tetrahedron Lett. 1992, 33, 2253-2256.
30. 3 was carried out. The product (2R,3R)-2,3-dihydro-3,5-dimethyl-2-phenyl-4(1H)pyranone was isolated in very high endo selectivity (endo:exo 98:2).