The brucine N-oxide-promoted asymmetric Pauson-Khand reaction

Tetrahedron Letters

Volumn 41, Issue 17, 2000, Pages 3229-3233

  Kerr, William J ^a   Lindsay, David M ^a   Rankin, Elaine M ^a   Scott, James S ^a   Watson, Stephen P ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Amine N oxides; Asymmetric synthesis; Cobalt and compounds; Cyclopentenones; Pauson Khand reactions

Indexed keywords

ACETONE; AMINE OXIDE; BRUCINE; COBALT DERIVATIVE; CYCLOPENTENONE DERIVATIVE; ETHANE; OXIDE; SOLVENT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 0034701526     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00357-9     Document Type: Article

References (23)

1. For reviews, see: (a) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297.
2. (b) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
3. (a) Shambayati, S.; Crowe, W. E.; Schreiber, S. Tetrahedron Lett. 1990, 31, 5289.
4. (b) Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S. E. Synlett 1991, 204.
5. (c) Gordon, A. R.; Johnstone, C.; Kerr, W. J. Synlett 1995, 1083.
6. See, for example, Ref. 5 in Donkervoort, J. G.; Gordon, A. R.; Johnstone, C.; Kerr, W. J.; Lange, U. Tetrahedron 1996, 52, 7391.
7. For a review, see: Ingate, S. T.; Marco-Contelles, J. Org. Prep. Proc. Int. 1998, 30, 121.
8. (a) Hay, A. M.; Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Organometallics 1995, 14, 4986.
9. (b) Kerr, W. J.; Kirk, G. G.; Middlemiss, D. J. Organomet. Chem. 1996, 519, 93.
10. See, for example: (a) Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A.; Bernardes, V.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F. J. Am. Chem. Soc. 1994, 116, 2153.
11. (b) Montenegro, E.; Poch, M.; Moyano, A.; Pericàs, M. A.; Riera, A. Tetrahedron Lett. 1998, 39, 335.
12. (a) Park, H.-J.; Lee, B. Y.; Kang, Y. K.; Chung, Y. K. Organometallics 1995, 14, 3104.
13. (b) Rutherford, D. T.; Christie, S. D. R. Tetrahedron Lett. 1998, 39, 9805.
14. Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Synlett 1995, 1085.
15. Since our initial communication, Derdau et al. has reported a study of several chiral amine N-oxide promoters, all of which afford lower enantioselectivities than brucine N-oxide: Derdau, V.; Laschat, S.; Jones, P. G. Heterocycles 1998, 48, 1445.
16. All new compounds exhibited satisfactory analytical and spectral data.
17. Other chiral N-oxide promoters currently under investigation show differing selectivity profiles from brucine N-oxide. These studies will be reported in due course.
18. (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
19. (b) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 5793.
20. (c) Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
21. (d) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7637.
22. (e) Belanger, D. B.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7641.
23. (f) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384.