Enantioselective Diels-Alder reactions of optically active (buta-1,3-dien-2-yl)(salen)cobalt(iii) complexes

European Journal of Organic Chemistry

Volumn , Issue 12, 2001, Pages 2273-2282

  Chapman, John J ^b   Day, Cynthia S ^a   Welker, Mark E ^a  

^a WAKE FOREST UNIVERSITY   (United States)

^b Lorillard Research Center   (United States)

Author keywords

Asymmetric synthesis; Cobalt; Cycloadditions; N ligands

Indexed keywords

ALCOHOL; COBALT COMPLEX; SODIUM BOROHYDRIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; ENANTIOMER; OPTICAL ROTATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0034970977     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200106)2001:12<2273::AID-EJOC2273>3.0.CO;2-I     Document Type: Article

References (33)

1. For a review of our work in cobaltoxime chemistry see: M. W. Wright, H. L. Stokes, B. M. Richardson, T. A. Adams, T. L. Smalley, S. P. Vaughn, G. J. Lohr, M. E. Welker, L. Liable-Sands, A. L. Rheingold, Advances in Cycloaddition (Ed.: M. Lautens), JAI Press, Greenwich, CT, 1997, vol. 4, p. 149.
2. J. J. Chapman, M. E. Welker, Organometallics 1997, 16, 747.
3. J. J. Chapman, C. S. Day, M. E. Welker, Organometallics 2000, 19, 1615.
4. For a recent review see: E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 389.
5. For some examples of related reactions with α-bromoacrolein as dienophile see: - [4a] M. E. Bruin, E. P. Kündig, Chem. Commun. 1998, 2635.
6. [4b] Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 110, 5502.
7. Kündig has reported the use of an in situ generated chiral (o-quinodimethane)chromium complex (a diene rather than dienyl complex) that participates in Diels-Alder reactions: E. P. Kündig, J. Leresche, L. Saudan, G. Bernardinelli, Tetrahedron 1996, 52, 7363.
8. For a recent review see: E. J. Corey, A. Guzman-Perez, Angew. Chem. Int. Ed. 1998, 37, 389.
9. For some examples of related reactions with α-bromoacrolein as dienophile see: [6a] M. E. Bruin, E. P. Kundig, Chem. Commun. 1998, 2635.
10. [6b] Y. Hayashi, J. J. Rohde, E. J. Corey, J. Am. Chem. Soc. 1996, 110, 5502.
11. T. S. Powers, W. Jiang, J. Su, W. D. Wulff, J. Am. Chem. Soc. 1997, 119, 6438.
12. J. Barluenga, R.-M. Canteli, J. Florez, S. Garcia-Granda, A. Gutierrez-Rodriguez, E. Martin, J. Am. Chem. Soc. 1998, 120, 2514.
13. [9a] B. Weyerhausen, M. Nieger, K. H. Dötz, J. Org. Chem. 1999, 64, 4206.
14. [9b] K. H. Dotz, D. Bottcher, M. Jendro, J. Organometal. Chem. 1999, 583, 34.
15. [10a] J. F. Larrow, E. N. Jacobsen, Org. Synth. 1997, 75, 1.
16. [10b] J. F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, C. M. Zepp, J. Org. Chem. 1994, 59, 1939.
17. W. H. Leung, E. Y. Y. Chan, E. K. F. Chow, I. D. Williams, S. M. Peng, J. Chem. Soc., Dalton Trans. 1996, 1229.
18. [12a] M. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 227, 936.
19. [12b] E. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773.
20. [12c] D. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147.
21. [12d] S. Peukert, E. N. Jacobsen, Org. Lett. 1999, 1, 1245.
22. Y. J. Hu, X. D. Huang, Z. J. Yao, Y. C. Wu, J. Org. Chem. 1998, 63, 2456.
23. [14a] M. W. Wright, T. L. Smalley, M. E. Welker, A. L. Rheingold, J. Am. Chem. Soc. 1994, 116, 6777.
24. [14b] H. L. Stokes, B. M. Richardson, M. W. Wright, S. M. Vaughn, M. E. Welker, L. Liable-Sands, A. L. Rheingold, Organometallics 1995, 14, 5520.
25. [15a] G. Snatzke, P. C. Ho, Tetrahedron 1971, 27, 3645.
26. [15b] G. Snatzke, M. Kajtar, F. Werner-Zamojska, Tetrahedron 1972, 28, 281.
27. H. M. Walborsky, L. Barash, T. C. Davis, Tetrahedron 1963, 19, 2333.
28. E. J. Corey, W. Su, Tetrahedron Lett. 1988, 29, 3423.
29. H. Yamamoto, K. Furuta, Q. Gao, Org. Synth. 1995, 72, 86.
30. L. Paquette, M. J. Gardlik, J. Am. Chem. Soc. 1980, 102, 5016.
31. [20a] H. J. Backer, T. A. H. Blaas, Recl. Trav. Chim. Pays-Bas 1942, 61, 785.
32. [20b] T. E. Sample, L. F. Hatch, Org. Syn. Coll. Vol. VI 1988, 454.
33. L. Brandsma, H. D. Verkruijsse, Synthesis of Acetylenes, Allenes, and Cumulenes, Elsevier Publishing Co., New York, 1981, pp. 65, 171, 188.