Asymmetric synthesis of monodentate phosphine ligands based on chiral η6-Cr[arene] templates

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1379-1382

  Nelson, Scott G ^a   Hilfiker, Mark A ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000049256     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990929s     Document Type: Article

References (35)

1. For examples of optically active monodentate phosphine ligands and their use in asymmetric catalysis, see: (a) Morrison, J. D.; Burnett, R. E.; Aguiar, A. M.; Morrow, C. J.; Phillips, C. J. Am. Chem. Soc. 1971, 93, 1301-1303.
2. (b) Knowles, W. S.; Sabacky, M. J.; Vineyard, B. D. J. Chem. Soc., Chem. Commun. 1972, 10-11.
3. (c) Bogdanovic, B. Angew. Chem., Int. Ed. Engl. 1973, 12, 954-964.
4. (d) Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; p 105.
5. (e) Hamada, Y.; Seto, N.; Ohmori, H.; Hatano, K. Tetrahedron Lett. 1996, 37, 7565-7568.
6. (f) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Chem. Soc., Chem. Commun. 1997, 561-562.
7. (g) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
8. (h) Chen, Z.; Jiang, Q.; Zhu, G.; Xiao, D.; Cao, P.; Guo, C.; Zhang, X. J. Org. Chem. 1997, 62, 4521-4523.
9. (i) Hayashi, T.; Kawatsura, M.; Uozumi, Y. J. Am. Chem. Soc. 1998, 120, 1681-1687.
10. (j) Hayashi, T. J. Organomet. Chem. 1999, 576, 195-202 and references therein.
11. (k) Dai, X. D.; Virgil, S. Tetrahedron Lett. 1999, 40, 1245-1248.
12. (l) Graf, C. D.; Malan, C.; Harms, K.; Knochel, P. J. Org. Chem. 1999, 64, 5581-5588.
13. 6-Cr[arene] units, see: (a) Uemura, M.; Miyake, R.; Nishimura, H.; Matsumoto, Y.; Hayashi, T. Tetrahedron: Asymmetry 1992, 3, 213-216.
14. (b) Hayashi, Y.; Sakai, H.; Kaneta, N.; Uemura, M. J. Organomet. Chem. 1995, 503, 143-148.
15. (c) Ariffin, A.; Blake, A. J.; Li, W.-S.; Simpkins, N. S. Synlett 1997, 1453-1455.
16. For a review of syntheses of optically active Cr[arene] complexes, see: Bolm, C.; Muñiz, K. Chem. Soc. Rev. 1999, 28, 51-59.
17. Kündig, E. P.; Quattropani, A. Tetrahedron Lett. 1994, 35, 3497-3500.
18. 2O/pentane) afforded 6 in ≥ 95% ee.
19. (a) Uemura, M.; Nishimura, H.; Hayashi, T. J. Organomet. Chem. 1994, 473, 129-137.
20. (b) Uemura, M.; Kamikawa, K. J. Chem. Soc., Chem. Commun. 1994, 2697-2698.
21. (c) Watanabe, T.; Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1995, 36, 6695-6698.
22. The assignment of 7a-c as adopting the thermodynamically favored exo conformation is consistent with the structure of related Cr[arene] complexes prepared under thermodynamic control; see: Uemura, M.; Nishimura, H.; Kamikawa, K.; Shiro, M. Inorg. Chim. Acta 1994, 222, 63-70. The conformation of the 1-naphthyl derivative 7a was further established by X-ray crystal structure determination of the related phosphine complex 10. See the Supporting Information for full details.
23. The observed exo:endo ratio in 7c appears to represent the groundstate conformer population, as the isomers can be interconverted at elevated temperatures while cooling reestablishes the original 2.3:1 exo:endo ratio.
24. Semmelhack, M. F. Nucleophilic Addition to Arene-Metal Complexes. In Comprehensive Organic Synthesis; Trost; B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 517-549.
25. NAr2 reactions of chiral Cr[arene] complexes, see: Kamikawa, K.; Uemura, M. Tetrahedron Lett. 1996, 37, 6359-6362.
26. Carbamates 7a-e were reacted with the lithiodiphenylphosphine (2 equiv) in THF (0.16 M) at -78°C. After the mixtures were stirred for 20 min, they were warmed to ambient temperature. After 12 h, the reaction mixtures were filtered through a silica gel pad and purified by column chromatography (hexanes/ethyl acetate). The optically active triarylphosphine complexes 9a-e are highly crystalline, air-stable solids.
27. 8 Carbon Ligands. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: New York, 1982; Vol. 3, pp 953-1077.
28. (b) Morris, M. J. Arene and Heteroarene Complexes of Chromium, Molybdenum, and Tungsten. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 5, pp 471-549.
29. Mason, R.; Russell, D. R. J. Chem. Soc., Chem. Commun. 1966, 26-28.
30. For asymmetric allylic substitution reactions catalyzed by monophosphine-palladium catalysts, see ref le,f,h-l.
31. For reviews of catalyzed allylic substitution reactions, see: (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.
32. (b) Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364.
33. (c) Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
34. Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145.
35. Similar enantioselection is obtained in alkylation of 11 catalyzed by 5 mol % 10 employing the sodium salt of dimethyl malonate (86% ee).