Reductive cyclodimerisation of Arylmethylidenemalononitriles Promoted by Sm/Incl 3 ·4H 2 O System in Aqueous Media: Highly Stereoselective Synthesis of Cyclopentamine Derivatives †
Free accessOtherFirst published online September, 2002
Reductive cyclodimerisation of Arylmethylidenemalononitriles Promoted by Sm/Incl 3 ·4H 2 O System in Aqueous Media: Highly Stereoselective Synthesis of Cyclopentamine Derivatives †
In the presence of active indium produced in situ by the Sm/InCl3·4H2O system, arylmethylidenemalononitriles undergo reductive cyclodimerisation to afford cyclopentamine derivatives with high stereoselectivity under mild conditions in aqueous media.
LubineauA., AugeJ., and QueneauY., Synthesis, 1994, 741; C. J. Li, Chem. Rev. 1993, 93, 2023; C. J. Li, Tetrahedron, 1996, 52, 5643.
2.
PaquetteL.A., and MitzelT. M., J. Am. Chem. Soc., 1996, 118, 1931; L. A. Paquette and P. C. Lobben, J. Am. Chem. Soc., 1996, 118, 1917; C. J. Li, D. L. Chen, Y. Q. Lu, J. X. Haberman and J. T. Megue. J. Am. Chem. Soc, 1996, 118, 4216.
3.
LiC.J., and ChanT. H., Tetrahedron Lett., 1991, 32, 7071; T. H. Chan and M. B. Isaac, Pure. Appl. Chem., 1996, 68, 919.
4.
(a) LiC.J., Chem. Rev., 1993, 93, 2023; (b) P. Cintas, Synlett, 1995, 1087; (c) C. J. Li and T. H. Chan, Tetrahedron, 1999, 55, 11149; (d) K. K. Chauhan and C. G. Frost, J. Chem. Soc., Perkin Trans. 1, 2000, 3015; (e) B. C. Ranu, Eur. J. Org. Chem., 2000, 2347; (f) L. A. Paquette, B. E. Kern and J. M. Andino, Tetrahedron Lett., 1999, 40, 4129; (g) J. Auge, N. L. Germain and A. T. Woaye, Tetrahedron Lett., 1999, 40, 9245; (h) T. P. Loh, J. M. Huang, K. C. Xu, S. H. Goh and J. J. Vittal, Tetrahedron Lett., 2000, 41, 6511; (i) F. A. Khan and B. Prabhudas, Tetrahedron, 2000, 56, 7595; (j) G. C. Lloyd-Jones, M. Murray, R. A. Stentiford and P. A. Worthington, Eur. J. Org. Chem., 2000, 975; (k) P. H. Lee, H. Ahn, K. Lee, S. Y. Sung and S. Kim, Tetrahedron Lett., 2001, 42, 37.
5.
RanuB.C., DuttaJ., and GuchhaitS. K., Org. Lett., 2001, 3, 2603 and references cited therein.
6.
(a) RiekeR.D., Science, 1989, 246, 1260; (b) R. D. Rieke, Top. Curr. Chem., 1975, 59, 1; (c) R. D. Rieke, Acc. Chem. Res., 1977, 10, 301.
