Chiral bipyridine–copper(II) complex. Crystal structure and catalytic activity in asymmetric cyclopropanation

Abstract

A chiral bipyridine–copper(II) complex has been prepared and its crystal structure determined. The structure involves a CuN₂Cl₂ compressed tetrahedral stereochemistry. Chiral bipyridine complexes of copper-(I) and -(II) triflate are active catalysts for asymmetric cyclopropanation of alkenes with enantiomeric excesses up to 92%.

References

1. A. Togni and L. M. Venanzi, Angew. Chem., Int. Ed. Engl., 1994, 66, 497.
2. M. P. Doyle, in Catalytic asymmetric synthesis, ed. I. Ojima, VCH, Weinheim, 1993, p. 63.
3. D. A. Evans, K. A. Woerpel, M. M. Hinman and M. F. Faul, J. Am. Chem. Soc., 1991, 113, 726; R. E. Lowenthal, A. Abiko and S. Masamune, Tetrahedron Lett., 1990, 31, 6005; T. G. Gant, M. C. Noe and E. J. Corey, Tetrahedron Lett., 1995, 36, 8745; S.-G. Kim, C.-W. Cho and K. H. Ahn, Tetrahedron: Asymmetry, 1997, 8, 1023.
4. H. Fritschi, U. Leutenegger and A. Pfaltz, (a)Helv. Chim. Acta, 1988, 71, 1553; (b)Angew. Chem., Int. Ed. Engl., 1986, 25, 1005.
5. H. Nozaki, S. Moriuti, H. Takaya and R. Noyori, Tetrahedron Lett., 1966, 5239; T. Aratani, Pure Appl. Chem., 1985, 57, 1839; Z. Li, R. W. Quan and E. N. Jacobsen, J. Am. Chem. Soc., 1995, 117, 5889.
6. K. Ito, S. Tabuchi and T. Katsuki, Synlett., 1992, 575; K. Ito and T. Katsuki, Tetrahedron Lett., 1993, 34, 2661; Synlett., 1993, 638.
7. C. Bolm, M. Zender and D. Bur, Angew. Chem., Int. Ed. Engl., 1990, 29, 205.
8. J. Hall, J.-M. Lehn, A. DeCian and J. Fischer, Helv. Chim. Acta, 1991, 74, 1.
9. D. A. Evans, K. A. Woerpel and M. J. Scott, Angew. Chem., Int. Ed. Engl., 1992, 31, 430.
10. J. Blankley, F. J. Sauter and H. O. House, Org. Synth., 1973, Coll. Vol. V, 258.
11. B. J. Hathaway, in Comprehensive Coordination Chemistry, eds. G. Wilkinson, R. P. Gillard and J. A. McCleverty, Pergamon, Oxford, 1987, vol. 5, ch. 53, p. 533.
12. J. Foley, S. Tyagi and B. J. Hathaway, J. Chem. Soc., Dalton Trans., 1984, 1.
13. C. B. Castellani, G. Gatti and R. Millini, Inorg. Chem., 1984, 23, 4004; G. Druhan and B. J. Hathaway, Acta Crystallogr., Sect. B, 1979, 35, 344; N. J. Ray and B. J. Hathaway, Acta Crystallogr., Sect. B, 1978, 34, 3224.
14. W. M. Davis, A. Zask, K. Nakanishi and S. J. Lippard, Inorg. Chem., 1985, 24, 3737; E. D. Gouge and J. F. Geldard, Inorg. Chem., 1978, 17, 270; H. Yokoi and A. W. Addison, Inorg. Chem., 1977, 16, 1341.