Recoverable chiral sulfoxide: remote asymmetric induction in Lewis acid-promoted Diels–Alder reaction of chiral sulfinyl-substituted pyrrolyl α,β-unsaturated enones

Abstract

1-[2-( p-Tolylsulfinyl)]pyrrolyl α,β-unsaturated enones served as efficient dienophiles in the Diels–Alder reaction, where the use of aluminium chloride or a lanthanide triflate effected the cycloaddition with cyclopentadiene, affording the endo adduct with high diastereoselectivity. In particular, for the sulfinyl dienophile, the chiral auxiliary (i.e. the sulfinyl pyrrole) was recovered after use without any loss of optical purity.

References

1. For reviews, see M. Mikołajczk, J. Drabowicz and P. Kiełbasiński, Chiral Sulfur Reagents: Applications in Asymmetric and Stereoselective Synthesis, CRC Press, Boca Raton, 1997, Ch. 3; Y. Arai, Yuki Gosei Kagaku Kyokaishi, 1998, 56, 798 (Chem. Abstr., 1998, 129, 289714); S. M. Allin, S. J. Shuttleworth and P. C. B. Page, Organosulfur Chem., 1998, 2, 97; S. M. Allin and P. C. B. Page, Org. Prep. Proced. Int., 1998, 30, 147; M. C. Carreño, Chem. Rev., 1995, 95, 1717; Y. Arai and T. Koizumi, Sulfur Rep., 1993, 15, 41; Rev. Heteroatom Chem., 1992, 6, 202; O. De Lucchi and L. Pasquato, Tetrahedron, 1988, 44, 6755.
2. F. M. Hauser, S. R. Ellenberger, J. C. Clardy and L. S. Bass, J. Am. Chem. Soc., 1984, 106, 2458.
3. S. Braverman, in The Chemistry of Sulphones and Sulphoxides, ed. S. Patai, Z. Rappoport and C. J. M. Stirling, Wiley, Chichester, 1988, pp. 717–753.
4. G. Solladié, F. Colobert and F. Somny, Tetrahedron Lett., 1999, 40, 1227; G. Solladié, G. Hanquet and C. Rolland, Tetrahedron Lett., 1999, 40, 177; Y. Arai, A. Suzuki, T. Masuda, Y. Masaki and M. Shiro, Chem. Pharm. Bull., 1996, 44, 1765; C. Iwata, Y. Moritani, K. Sugiyama, M. Fujita and T. Imanishi, Tetrahedron Lett., 1987, 28, 2255.
5. N. Maezaki, T. Shogaki, T. Imamura, K. Tokuno, K. Ohkubo, T. Tanaka and C. Iwata, Chem. Pharm. Bull., 1998, 46, 837.
6. Y. Arai, A. Suzuki, T. Masuda, Y. Masaki and M. Shiro, J. Chem. Soc., Perkin Trans. 1, 1995, 2913; P. C. B. Page, M. J. McKenzie, S. M. Alin, E. W. Collinton and R. A. E. Carr, Tetrahedron, 1995, 51, 1285; Y. Arai, T. Masuda, Y. Masaki and T. Koizumi, Heterocycles, 1994, 38, 1751; P. C. B. Page, A. M. Z. Slawin, D. Westwood and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1989, 185; P. C. B. Page, S. S. Klair and D. Westwood, J. Chem. Soc., Perkin Trans. 1, 1989, 2441.
7. M. C. Carreño, M. P. González, M. Ribagorda and J. Fischer, J. Org. Chem., 1997, 62, 6758; P. C. B. Page, J. C. Prodger, M. B. Hursthouse and M. Mazid, J. Chem. Soc., Perkin Trans. 1, 1990, 167.
8. (a) Y. Arai, T. Masuda, Y. Masaki and M. Shiro, J. Chem. Soc., Perkin Trans. 1, 1996, 759; Y. Arai, T. Masuda and Y. Masaki, Chem. Pharm. Bull., 1998, 46, 1078; (b) M. C. Carreño, M. P. González and K. N. Houk, J. Org. Chem., 1997, 62, 9128; Y. Arai, T. Masuda, Y. Masaki and M. Shiro, Tetrahedron: Asymmetry, 1996, 7, 1199; M. C. Carreño, J. L. García Ruano, M. A. Toledo and A. Urbano, Tetrahedron Lett., 1994, 35, 9759; M. C. Carreño, J. L. García Ruano and A. Urbano, Tetrahedron Lett., 1989, 30, 4003.
9. For a preliminary report of this research, see Y. Arai, T. Masuda and Y. Masaki, Chem. Lett., 1997, 145.
10. L. A. Carpino and D. E. Barr, J. Org. Chem., 1966, 31, 764.
11. (a) I. Hasan, E. R. Marinelli, L. C. Lin, F. W. Fowler and A. B. Levy, J. Org. Chem., 1981, 46, 157; (b) W. Chen, E. K. Stephenson, M. P. Cava and Y. A. Jackson, Org. Synth., 1992, 70, 151; (c) D. J. Chadwick and S. T. Hodgson, J. Chem. Soc., Perkin Trans. 1, 1982, 1833.
12. L. D. Girodier, C. Maignan and F. Rouessac, Tetrahedron: Asymmetry, 1995, 6, 2045; 1992, 3, 857.
13. D. E. Ward and C. K. Rhee, Tetrahedron Lett., 1991, 32, 7165.
14. J. Drabowicz and M. Mikołajczyk, Synthesis, 1978, 138.
15. D. A. Evans, K. T. Chapman and J. Bisaha, J. Am. Chem. Soc., 1988, 110, 1238.
16. Indirect recovery of the chiral sulfoxides; R. J. Butlin, I. D. Linney, M. F. Mahon, H. Tye and M. Wills, J. Chem. Soc., Perkin Trans. 1, 1996, 95; R. J. Butlin, I. D. Linney, D. J. Critcher, M. F. Mahon, K. C. Molloy and M. Wills, J. Chem. Soc., Perkin Trans. 1, 1993, 1581; Y. Arai, M. Matsui and T. Koizumi, J. Chem. Soc., Perkin Trans. 1, 1990, 1233; B. M. Eschler, R. K. Haynes, S. Kremmydas and D. D. Ridley, J. Chem. Soc., Chem. Commun., 1988, 137.
17. For recent reviews, see R. E. Gawley and J. Aubé, Principles of Asymmetric Synthesis, Pergamon, Oxford, 1996, pp. 263–285; J. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, Wiley, New York, 1995, pp. 536–592; H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007; K. Narasaka, Synthesis, 1991, 1.
18. S. D. Kahn and W. J. Hehre, Tetrahedron Lett., 1986, 27, 6041; J. Am. Chem. Soc., 1986, 108, 7399.
19. L. Gong and A. J. Streitwieser, Jr, J. Org. Chem., 1990, 55, 6235.
20. N. N. Schwartz and J. H. Blumbergs, J. Org. Chem., 1964, 29, 1976.