Asymmetric synthesis of sulfinyl-substituted arene chromium tricarbonyl complexes

Abstract

The synthesis of (SRS_S )-[(phenylsulfinyl)benzene] chromium tricarbonyl 5 and (SRS_S )-[( p-tolylsulfinyl)benzene] chromium tricarbonyl 6 is achieved via a nucleophilic displacement reaction between the anion derived from (benzene) chromium tricarbonyl 9 and a suitable sulfinate ester. Replacing the sulfinate ester with a chiral sulfinyl-transfer reagent allows the isolation of the non-racemic sulfinyl-substituted complexes with good enantioselectivities (ee 80–89%) under optimised conditions. The use of Kagan’s cyclic sulfite methodology for the synthesis of an enantiomerically pure tert-butylsulfinyl complex is unsuccessful, but results in the identification of a novel fragmentation–isomerisation process of the intermediate sulfinate.

References

1. (a) A. Solladié-Cavallo, G. Solladié and E. Tsamo, J. Org. Chem., 1979, 44, 4189; (b) A. Alexakis, P. Mangeney, I. Marek, F. Rose-Munch, E. Rose, A. Semra and F. Robert, J. Am. Chem. Soc., 1992, 114, 8288; (c) S. G. Davies and C. L. Goodfellow, J. Chem. Soc., Perkin Trans. 1, 1989, 192; L. A. Bromley, S. G. Davies and C. L. Goodfellow, Tetrahedron: Asymmetry, 1991, 2, 139.
2. K. Nakamura, K. Ishihara, A. Ohno, M. Uemura, H. Nishimura and Y. Hayashi, Tetrahedron Lett., 1990, 31, 3603; S. Top, G. Jaouen, J. Gillois, C. Baldoli and S. Maiorana, J. Chem. Soc., Chem. Commun., 1988, 1284.
3. M. Uemura, T. Minami, K. Hirotsu and Y. Hayashi, J. Org. Chem., 1989, 54, 469; M. Uemura, T. Kobayashi, T. Minami and Y. Hayashi, Tetrahedron Lett., 1986, 27, 2479; M. Uemura, T. Kobayashi, K. Isobe, T. Minami and Y. Hayashi, J. Org. Chem., 1986, 51, 2859 See also ref. 16.
4. Y. Kondo, J. R. Green and J. Ho, J. Org. Chem., 1991, 56, 7199; J. Aubé, J. A. Heppert, M. L. Milligan, M. J. Smith and P. Zenk, J. Org. Chem., 1992, 57, 3563; Y. Kondo, J. R. Green and J. Ho, J. Org. Chem., 1993, 58, 6182; A. Alexakis, T. Kanger, P. Mangeney, F. Rose-Munch, A. Perrotey and E. Rose, Tetrahedron: Asymmetry, 1995, 6, 47; S. G. Davies and W. E. Hume, J. Chem. Soc., Chem Commun., 1995, 251; J. W. Han, S. U. Son and Y. K. Chung, J. Org. Chem., 1997, 62, 8264.
5. D. A. Price, N. S. Simpkins, A. M. MacLeod and A. P. Watt, J. Org. Chem., 1994, 59, 1961 (Tetrahedron Lett., 1994, 35, 6159); E. P. Kundig and A. Quattropani, Tetrahedron Lett., 1994, 35, 3497; M. Uemura, Y. Hayashi and Y. Hayashi, Tetrahedron: Asymmetry, 1994, 5, 1427; H. G. Schmalz and K. Schellhaas, Tetrahedron Lett., 1995, 36, 5515; A. Alexakis, T. Kanger, P. Mangeney, F. Rose-Munch, A. Perrotey and E. Rose, Tetrahedron: Asymmetry, 1995, 6, 2135; M. J. Siwet and J. R. Green, Chem. Commun., 1996, 2359; R. A. Ewin, A. M. MacLeod, D. A. Price, N. S. Simpkins and A. P. Watt, J. Chem. Soc., Perkin Trans. 1, 1997, 401; A. Quattropani, G. Bernardinelli and E. P. Kunig, Helv. Chim. Acta, 1999, 82, 90.
6. A. Perez-Encabo, S. Perrio, A. M. Z. Slawin, S. E. Thomas, A. T. Wierzchleyski and D. J. Williams, J. Chem. Soc., Chem. Commun., 1993, 1059 (J. Chem. Soc., Perkin Trans. 1, 1994, 629).
7. S. L. Griths, S. Perrio and S. E. Thomas, Tetrahedron: Asymmetry, 1994, 5, 545, 1847.
8. S. G. Davies, T. Loveridge and J. M. Clough, J. Chem. Soc., Chem. Commun., 1995, 817.
9. J.-H. Youn and R. Herrmann, Tetrahedron Lett., 1986, 27, 1493; H. F. Herbrandson, R. T. Dickerson and J. Weinstein, J. Am. Chem. Soc., 1956, 78, 2576; M. Mikolajcyzk and J. Drabowicz, Synthesis, 1974, 124.
10. R. J. Card and W. S. Trahanovsky, J. Org. Chem., 1980, 45, 2555, 2560.
11. Isolation of this material was achieved by washing the silica frit with methanol. However, ¹H NMR spectroscopic analysis resulted in a complex spectrum with no identifiable peaks.
12. D. A. Evans, M. M. Faul, L. Colombo, J. J. Bisaha, J. Clardy and D. Cherry, J. Am. Chem. Soc., 1992, 114, 5977.
13. M. Deshmukh, E. Dunach, S. Juge and H. B. Kagan, Tetrahedron Lett., 1984, 25, 3467; 1985, 26, 402.
14. On one occasion three recrystallisations of “(S_S)”-5(ee 67%) from hexane-toluene (2:1) furnished mother liquors with an enhanced ee of 91%.
15. F. Rebière, O. Samuel, L. Ricard and H. B. Kagan, J. Org. Chem., 1991, 56, 5991.
16. L. E. Orgel, Inorg. Chem., 1962, 1, 25.
17. F. G. Bordwell and B. M. Pitt, J. Am. Chem. Soc., 1955, 77, 572; B. M. Trost and D. P. Curran, Tetrahedron Lett., 1981, 22, 1287; C. Y. Meyers, W. S. Matthews, G. J. McCollum and J. C. Branca, Tetrahedron Lett., 1974, 1105.
18. For a review of work published in this area see: S. Braverman, in The Chemistry of Sulfoxides and Sulfones, ed. S. Patai, Z. Rappoport and C. J. M. Stirling, Wiley and Sons, Chichester, 1988, p. 665.
19. D. Darwish and R. McLaren, Tetrahedron Lett., 1962, 1231.
20. E. Ciuffarin, M. Isola and A. Fava, J. Am. Chem. Soc., 1968, 90, 3594.
21. D. F. Shriver and M. A. Dreszdon, The Manipulation of Air Sensitive Compounds, Wiley, New York, 1986, 2nd edn.
22. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923.
23. C. A. L. Mahaffy and P. L. Pauson, Inorg. Synth., 1979, 19, 154.
24. K. K. Andersen, Tetrahedron Lett., 1962, 93.