Reversing the Stereoselectivity of the Intermolecular Pauson-Khand Reaction: Formation of endo-Fused Norbornadiene Adducts

Organic Letters

Volumn 4, Issue 7, 2002, Pages 1205-1208

  Rios, Ramon ^a   Pericàs, Miquel A ^a   Moyano, Albert ^a   Maestro, Miguel A ^b   Mahía, José ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF A CORUÑA   (Spain)

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ARTICLE;

EID: 0005993742     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025649i     Document Type: Article

References (20)

1. Recent reviews on the Pauson-Khand reaction: (a) Schore, N. E. Org. React. 1991, 40, 1-90.
2. (b) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911-914.
3. (c) Buchwald, S. L.; Hicks, F. A. In Comprehensive Asymmetric Catalysis, Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. II, pp 491-510.
4. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283.
5. (e) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem. Eur. J. 2001, 7, 1589-1595.
6. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977-981.
7. Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436-5438.
8. (a) Rutherford, D. T.; Christie, S. D. R. Tetrahedron Lett. 1998, 39, 9805-9808.
9. (b) Fletcher, A. J.; Rutherford, D. T.; Christie, S. D. R. Synlett 2000, 1040-1042.
10. (a) Fonquerna, S.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Am. Chem. Soc. 1997, 119, 10225-10226.
11. (b) Fonquerna, S.; Rios, R.; Moyano, A.; Pericàs, M. A.; Riera, A. Eur. J. Org. Chem. 1999, 3459-3478.
12. Albiez, T.; Bantel, H.; Vahrenkamp, H. Chem. Ber. 1990, 123, 1805-1810.
13. Further experiments indicate that alkyl substituents other than methyl can be used in this reaction. Thus, 4,4-dimethyl-3-(non-8-ene-2-ynoyl)-1,3-oxazolidin-2-one affords the corresponding heterobimetallic (Mo-Co) complex in 83% yield.
14. 3); MS (posit. electrospray, MeOH) m/z 544.2 [M + 1].
15. 4 [M + H] 302.1379, found 302.1392.
16. 2,6]deca-3,8-dien-5-ones have been described in the literature. See: (a) Verlaak, J. M. J.; Klunder, A. J. M.; Zwanenburg, B. Tetrahedron Lett. 1982, 23, 5463-5466.
17. (b) Mal, D.; N. Hazra, N. K. J. Chem. Soc,. Chem. Commun. 1996, 1181-1182.
18. (c) Lee, B. H.; Clothier, M. F.; Dutton, F. E.; Clonder, G. A.; Johnson, S. S. Bioorg. Med. Chem. Lett. 1998, 8, 3317-3320.
19. Recently, an stereocomplementary intramolecular Pauson-Khand reaction that primarily affords endo-6-alkoxybicyclo[3.3.0]oct-1-en-3-ones instead of the 6-exo ones has been disclosed: (a) Adrio, J.; Rivero, M. R.; Carretero, J. C. Angew. Chem., Int. Ed. 2000, 39, 2906-2909.
20. (b) Adrio, J.; Rivero, M. R.; Carretero, J. C. Chem. Eur. J. 2001, 7, 2435-2448.