On the mechanism of remote induction using (5-alkoxypent-2-enyl)stannanes: trapping the intermediate allyltin trihalides by phenyllithium and the X-ray crystal structure of [(2SR,3RS)-1-(4-bromobenzoyloxy)-2-methylpent-3-yl]-(triphenyl)stannane

Abstract

Allyltin trihalides, intermediates in tin(IV) halide promoted reactions of 5-alkoxy-4-methylpent-2-enyl(triphenyl)- stannanes with aldehydes which proceed with 1,5-induction, have been trapped by phenyllithium to give [(3RS,4SR)-5-alkoxy-4-methylpent-1-en-3-yl](triphenyl)stannanes.

References

1. E. J. Thomas, Chem. Commun., 1997, 411.
2. J. S. Carey and E. J. Thomas, Synlett, 1992, 585.
3. A. H. McNeill and E. J. Thomas, Tetrahedron Lett., 1990, 31, 6239; V. J. Jephcote, A. J. Pratt and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1989, 1521.
4. J. S. Carey, T. S. Coulter and E. J. Thomas, Tetrahedron Lett., 1993, 34, 3933.
5. V. J. Jephcote and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1991, 429.
6. P. T. Beurskens, G. Admiraal, G. Beurskens, W. P. Bosman, S. Garcia-Granda, R. O. Gould, J. M. M. Smits and C. Smykalla, The DIRDIF Program System, 1992, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands.
7. TEXSAN: Crystal Structure Analysis Package, Molecular Structure Corporation, 1985 and 1992.