Catalytic Asymmetric Bromination and Chlorination of O-Ketoesters

Chemistry - A European Journal

Volumn 10, Issue 9, 2004, Pages 2133-2137

  Marigo, Mauro ^a   Kumaragurubaran, Nagaswami ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Asymmetric catalysis; Brominitioh; Chlorination

Indexed keywords

CATALYSIS; CATALYSTS; CHLORINATION; COORDINATION REACTIONS; HALOGENATION; REACTION KINETICS; X RAY ANALYSIS;

BROMINATION; OPTICALLY ACTIVE PRODUCTS;

ESTERS;

BETA OXOCARBOXYLIC ACID ESTER; BISOXAZOLINECOPPER COMPLEX; COPPER COMPLEX; COPPER DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; BROMINATION; CHEMICAL STRUCTURE; CHIRALITY; CHLORINATION; ENANTIOSELECTIVITY; OPTICS; X RAY ANALYSIS;

EID: 2442584755     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305759     Document Type: Article

References (28)

1. For highlight see K. Muniz, Angew. Chem. 2001, 113, 1701; Angew. Chem. Int. Ed. 2001, 40, 1653.
2. For highlight see K. Muniz, Angew. Chem. 2001, 113, 1701; Angew. Chem. Int. Ed. 2001, 40, 1653.
3. a) L. Hintermann, A. Togni, Angew. Chem. 2000, 112, 4530; Angew. Chem. Int. Ed. 2000, 39, 4359;
4. a) L. Hintermann, A. Togni, Angew. Chem. 2000, 112, 4530; Angew. Chem. Int. Ed. 2000, 39, 4359;
5. b) S. Plana, I. Devillers, A. Togni, U. Rothisberger, Angew. Chem. 2002, 114, 1021; Angew. Chem. Int. Ed. 2002, 41, 979;
6. b) S. Plana, I. Devillers, A. Togni, U. Rothisberger, Angew. Chem. 2002, 114, 1021; Angew. Chem. Int. Ed. 2002, 41, 979;
7. c) R. Frantz, L. Hintermann, M. Perseghini, D. Brogginio, A. Togni, Org. Lett. 2003, 5, 1709.
8. Y. Hamashima, K. Yagi, H. Takano, L. Tamás, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 14530. See also: Y. Masashima, H. Takano, D. Hotta, M. Sodeoka, Org. Lett. 2003, 5, 3225.
9. Y. Hamashima, K. Yagi, H. Takano, L. Tamás, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 14530. See also: Y. Masashima, H. Takano, D. Hotta, M. Sodeoka, Org. Lett. 2003, 5, 3225.
10. D. Y. Kim, E. J. Park, Org. Lett. 2002, 4, 545.
11. L. Hintermann, A. Togni, Helv. Chim. Acta 2000, 83, 2425.
12. H. Wack, A. E. Taggi, A. M. Hafez, W. J. Drury III, T. Lectka, J. Am. Chem. Soc. 2001, 123, 1531.
13. For Lewis acid catalyzed halogenation reactions of 1,3-dicarbonyl compounds see, for example: D. Yang, Y.-L. Yan, B. Lui, J. Org. Chem. 2002, 67, 7429.
14. 2-bisoxazoline-Lewis acid complexes as catalysts see, for example: a) A. K. Ghosh, P. Mathivanen, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1;
15. b) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain, J. Thorhauge, Acc. Chem. Res. 1999, 32, 605;
16. c) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325.
17. For previous contributions where we have used the bisoxazolinecopper(II) complexes to first initiate the keto to enol transformation and then to catalyze an enantioselective electrophilic addition to the enolate form see: a) K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Commun. 2000, 2211;
18. b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080; Angew. Chem. Int. Ed. 2001, 40, 2992;
19. b) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. 2001, 113, 3080; Angew. Chem. Int. Ed. 2001, 40, 2992;
20. c) K. Juhl, K. A. Jørgensen, J. Am. Chem. Soc. 2002, 124, 2420;
21. d) M. Marigo, A. Kjærsgaard, K. Juhl, N. Gathergood, K. A. Jørgensen, Chem. Eur. J. 2003, 9, 2359;
22. e) M. Marigo, K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1405; Angew. Chem. Int. Ed. 2003, 42, 1367.
23. e) M. Marigo, K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1405; Angew. Chem. Int. Ed. 2003, 42, 1367.
24. The optically active chloro product below formed with 45% ee could be recrystallized to obtain an optical purity of 90% ee:
25. J. Thorhauge, M. Roberson, R. G. Hazell, K. A. Jørgensen, Chem. Eur. J. 2002, 8, 1888, and references therein.
26. X-ray crystallographic data are deposited with Cambridge Crystallographic Data Centre at no. CCDC 149317; see also: H. Audrian, J. Thorhauge, R. G. Hazell, K. A, Jørgensen, J. Org. Chem. 2000, 65, 4487.
27. J. Helleou, K. J. Kingston, G. A. Fallis, Synthesis 1984, 1014.
28. S. E. Denmark, C. M. Stiff, J. Org. Chem. 2000, 65, 5875.