Recognition-induced control of a Diels–Alder reaction

Abstract

The rational design of a system which is capable of controlling the stereochemical outcome of a Diels–Alder reaction between a maleimide and a furan is presented.

References

1. For excellent general reviews, see A. J. Kirby, Angew. Chem., Int. Ed. Engl., 1996, 35, 707; H. Dugas, Bioorganic Chemistry—A Chemical Approach to Enzyme Action, Springer-Verlag, New York, 3rd edn., 1996For some efficient examples, see M. W. Hosseini, J. M. Lehn, K. C. Jones, K. E. Plute, K. B. Mertes and M. P. Mertes, J. Am. Chem. Soc., 1989, 111, 6330; I. Huc, J. Pieters and J. Rebek, Jr., J. Am. Chem. Soc., 1994, 116, 10296; P. Tecilla, V. Jubian and A. D. Hamilton, Tetrahedron, 1995, 51, 435.
2. M. C. Carreno, J. L. G. Ruano and A. Urbano, J. Org. Chem., 1996, 61, 6136; D. S. Millan, T. T. Pham, J. A. Lavers and A. G. Fallis, Tetrahedron Lett., 1997, 38, 795; M. J. Lilly and M. S. Sherburn, Chem. Commun., 1997, 967; T. Wong, P. D. Wilson, S. Woo and A. G. Fallis, Tetrahedron Lett., 1997, 38, 7045; E. J. Bush and D. W. Jones, J. Chem. Soc., Perkin Trans. 1, 1997, 3531.
3. T. R. Kelly, V. S. Ekkundi and P. Meghani, Tetrahedron Lett., 1990, 31, 3381; S. C. Hirst and A. D. Hamilton, J. Am. Chem. Soc., 1991, 113, 382; C. J. Walter and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1995, 34, 217; H. L. Anderson and J. K. M. Sanders, J. Chem. Soc., Perkin Trans. 1, 1995, 2223; J. Rebek, Jr. and J. Kang, Nature, 1997, 385, 50; B. Wang and I. O. Sutherland, Chem. Commun., 1997, 1495.
4. Sim Fit, A Program for the Analysis of Kinetic Data, Version 1.0, G. von Kiedrowski, 1994.