¹H NMR study of the hydrolysis of N-acylhydroxy[²H]methylpyrroles

Abstract

KOH catalysed hydrolysis of the (S)- and (R)-N- (N-phthalylleucinyl)hydroxy[²H]methylpyrroles 6b and 6c, in CD₃CN containing 1 equiv. of (+)-sec-butylamine, proceeds by an initial N- to O-acyl transfer with retention of configuration at the labelled centre, followed by trapping of an azafulvene to give (S)- and (R)-sec-butylamino[²H]methylpyrroles 9b.

References

1. The Chemistry of Pyrroles, ed. A. R. Jones and G. P. Bean, Academic Press, London, 1977; Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon, Oxford, vol. 4, 1984; R. A. Barcock, N. A. Moorcroft and R. C. Storr, Tetrahedron Lett., 1993, 34, 1187.
2. A. D. Abell, B. K. Nabbs and A. R. Battersby, J. Am. Chem Soc., 1998, 120, 1741.
3. A. R. Battersby, C. J. R. Fookes, K. E. Gustafson-Potter, E. McDonald and G. W. T. Matcham, J. Chem. Soc., Perkin Trans. 1, 1982, 2427.
4. M. J. Ortega, E. Zubia, J. L. Carballo and J. Salva, Tetrahedron Lett., 1997, 38, 331.
5. S. Singh and G. P. Basmadjian, Tetrahedron Lett., 1997, 38, 6829.
6. J.-R. Schauder, S. Jendrezejewski, A. D. Abell, G. J. Hart and A. R. Battersby, J. Chem. Soc., Chem. Commun., 1987, 436.
7. A. D. Abell and J. C. Litten, Tetrahedron Lett., 1992, 33, 3005; A. D. Abell and J. C. Litten, Aust. J. Chem., 1993, 46, 1473.
8. J. Savrda, L. Chertanova and M. Wakselman, Tetrahedron, 1992, 33, 3005.