Stereoselective debromination of aryl-substituted vic-dibromide with indium metal

Abstract

Debromination of both meso and dl (erythro and threo) aryl-substituted vic-dibromides with indium metal in MeOH leads to trans-alkenes exclusively.

References

1. (a) E. L. Allred, B. R. Beck and K. J. Voorhees, J. Org. Chem., 1974, 39, 1426; (b) D. Landini, S. Quici and F. Rolla, Synthesis, 1975, 397; (c) D. Savoia, E. Tagliavini, C. Trombini and A. U. Ronchi, J. Org. Chem., 1982, 47, 876; (d) E. Baciocchi, in Chemistry of Functional Groups, Supplement D, Part 1, ed. S. Patai and H. Rappoport, Wiley, New York, 1983; (e) S. G. Davies and S. E. Thomas, Synthesis, 1984, 1027; (f) K. Yanada, R. Yanada and H. Meguri, J. Chem. Soc., Chem. Commun., 1990, 730; (g) J. M. Khurana and G. C. Maikap, J. Org. Chem., 1991, 56, 2582; (h) R. Yanada, N. Negoro, K. Yanada and T. Fujita, Tetrahedron Lett., 1996, 37, 9313; (i) C. Malanga, S. Mannucci and L. Lardicci, Tetrahedron, 1998, 54, 1021; (j) T. S. Butcher and M. R. Detty, J. Org. Chem., 1998, 63, 177.
2. P. Cintas, Synlett, 1995, 1087.
3. C. J. Li, D. L. Chen, Y. Q. Lu, J.-X. Haberman and J. T. Mague, J. Am. Chem. Soc., 1996, 118, 4216; V. J. Bryan and T. H. Chan, Tetrahedron Lett., 1996, 37, 5341; T.-P. Loh and X. R. Li, Tetrahedron Lett., 1997, 38, 869; M. B. Isaac and L. A. Paquette, J. Org. Chem., 1997, 62, 5333; X.-H. Yi, Y. Meng and C.-J. Li, Chem. Commun., 1998, 449.
4. S. Araki, A. Imai, K. Shimizu, M. Yamada, A. Mori and Y. Butsugan, J. Org. Chem., 1995, 60, 1841; B. C. Ranu and A. Majee, Chem. Commun., 1997, 1225; N. Fujiwara and Y. Yamamoto, J. Org. Chem., 1997, 62, 2318; T. P. Loh, D. S.-C. Ho, K.-C. Xu and K.-Y. Sim, Tetrahedron Lett., 1997, 38, 865.
5. T. Hudlicky, G. Sinai-Zingde and M. G. Natchus, Tetrahedron Lett., 1987, 28, 5287.
6. For indium promoted debromination of geminal dibromides, see: S. Araki and Y. Butsugan, J. Chem. Soc., Chem. Commun., 1989, 1286.