New optically active organotin compounds for heterogeneous bimetallic catalysis

Journal of Organometallic Chemistry

Volumn 520, Issue 1-2, 1996, Pages 101-106

  Lucas, Christine ^a   Santini, Catherine C ^a   Prinz, Martina ^a   Cordonnier, Marie Anne ^a   Basset, Jean Marie ^a   Connil, Marie Françoise ^b   Jousseaume, Bernard ^b  

^a CPE LYON   (France)

^b UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Heterogeneous bimetallic catalysis; Lithium stannate; Optically active organotin compounds; Tin

Indexed keywords

EID: 0030576376     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0022-328X(96)06270-5     Document Type: Article

References (41)

1. [1] M. Pereyre, J.-P. Quintard and A. Rahm, Tin in Organic-Synthesis, Butterworths, London, 1987; J.L. Wardell, in P.G. Harrison (ed.), Chemistry of Tin, Blackie, Glasgow, 1989, p. 315.
2. [1] M. Pereyre, J.-P. Quintard and A. Rahm, Tin in Organic-Synthesis, Butterworths, London, 1987; J.L. Wardell, in P.G. Harrison (ed.), Chemistry of Tin, Blackie, Glasgow, 1989, p. 315.
3. [2] B. Didillon, C. Houtmann, T. Shay, J.-P. Candy and J.-M. Basset, J. Am. Chem. Soc., 115 (1993) 9380.
4. [3] J.-P. Candy, B. Didillon, E.L. Smith, T. Shay and J.-M. Basset, J. Mol. Catal., 86 (1994) 179.
5. [4] A. Rahm and M. Pereyre, J. Organomet. Chem., 88 (1975) 179.
6. [5] S. Wattrelot, J.L. Parrain and J.P. Quintard, J. Org. Chem., 59 (1994) 7959; J.S. Carey and E.J. Thomas, Tetrahedron Lett., (1993) 3935; J.A. Marshall and Y.J. Tang, J. Org. Chem., 58 (1993) 3233; Y. Yamamoto, K. Kobayashi, H. Ohano and I.J. Katoda, J. Org. Chem., 57 (1992) 7003; M. Benechie and F. Khuong-Huu, Synlett, (1992) 266; A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 56 (1991) 6961; J.A. Marshall and D.V. Yashunsky, J. Org. Chem., 56 (1991) 5493; J.M. Chong and E.K. Mar, Tetrahedron, (1989) 7709.
7. [5] S. Wattrelot, J.L. Parrain and J.P. Quintard, J. Org. Chem., 59 (1994) 7959; J.S. Carey and E.J. Thomas, Tetrahedron Lett., (1993) 3935; J.A. Marshall and Y.J. Tang, J. Org. Chem., 58 (1993) 3233; Y. Yamamoto, K. Kobayashi, H. Ohano and I.J. Katoda, J. Org. Chem., 57 (1992) 7003; M. Benechie and F. Khuong-Huu, Synlett, (1992) 266; A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 56 (1991) 6961; J.A. Marshall and D.V. Yashunsky, J. Org. Chem., 56 (1991) 5493; J.M. Chong and E.K. Mar, Tetrahedron, (1989) 7709.
8. [5] S. Wattrelot, J.L. Parrain and J.P. Quintard, J. Org. Chem., 59 (1994) 7959; J.S. Carey and E.J. Thomas, Tetrahedron Lett., (1993) 3935; J.A. Marshall and Y.J. Tang, J. Org. Chem., 58 (1993) 3233; Y. Yamamoto, K. Kobayashi, H. Ohano and I.J. Katoda, J. Org. Chem., 57 (1992) 7003; M. Benechie and F. Khuong-Huu, Synlett, (1992) 266; A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 56 (1991) 6961; J.A. Marshall and D.V. Yashunsky, J. Org. Chem., 56 (1991) 5493; J.M. Chong and E.K. Mar, Tetrahedron, (1989) 7709.
9. [5] S. Wattrelot, J.L. Parrain and J.P. Quintard, J. Org. Chem., 59 (1994) 7959; J.S. Carey and E.J. Thomas, Tetrahedron Lett., (1993) 3935; J.A. Marshall and Y.J. Tang, J. Org. Chem., 58 (1993) 3233; Y. Yamamoto, K. Kobayashi, H. Ohano and I.J. Katoda, J. Org. Chem., 57 (1992) 7003; M. Benechie and F. Khuong-Huu, Synlett, (1992) 266; A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 56 (1991) 6961; J.A. Marshall and D.V. Yashunsky, J. Org. Chem., 56 (1991) 5493; J.M. Chong and E.K. Mar, Tetrahedron, (1989) 7709.
10. [5] S. Wattrelot, J.L. Parrain and J.P. Quintard, J. Org. Chem., 59 (1994) 7959; J.S. Carey and E.J. Thomas, Tetrahedron Lett., (1993) 3935; J.A. Marshall and Y.J. Tang, J. Org. Chem., 58 (1993) 3233; Y. Yamamoto, K. Kobayashi, H. Ohano and I.J. Katoda, J. Org. Chem., 57 (1992) 7003; M. Benechie and F. Khuong-Huu, Synlett, (1992) 266; A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 56 (1991) 6961; J.A. Marshall and D.V. Yashunsky, J. Org. Chem., 56 (1991) 5493; J.M. Chong and E.K. Mar, Tetrahedron, (1989) 7709.
11. [5] S. Wattrelot, J.L. Parrain and J.P. Quintard, J. Org. Chem., 59 (1994) 7959; J.S. Carey and E.J. Thomas, Tetrahedron Lett., (1993) 3935; J.A. Marshall and Y.J. Tang, J. Org. Chem., 58 (1993) 3233; Y. Yamamoto, K. Kobayashi, H. Ohano and I.J. Katoda, J. Org. Chem., 57 (1992) 7003; M. Benechie and F. Khuong-Huu, Synlett, (1992) 266; A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 56 (1991) 6961; J.A. Marshall and D.V. Yashunsky, J. Org. Chem., 56 (1991) 5493; J.M. Chong and E.K. Mar, Tetrahedron, (1989) 7709.
12. [5] S. Wattrelot, J.L. Parrain and J.P. Quintard, J. Org. Chem., 59 (1994) 7959; J.S. Carey and E.J. Thomas, Tetrahedron Lett., (1993) 3935; J.A. Marshall and Y.J. Tang, J. Org. Chem., 58 (1993) 3233; Y. Yamamoto, K. Kobayashi, H. Ohano and I.J. Katoda, J. Org. Chem., 57 (1992) 7003; M. Benechie and F. Khuong-Huu, Synlett, (1992) 266; A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 56 (1991) 6961; J.A. Marshall and D.V. Yashunsky, J. Org. Chem., 56 (1991) 5493; J.M. Chong and E.K. Mar, Tetrahedron, (1989) 7709.
13. [5] S. Wattrelot, J.L. Parrain and J.P. Quintard, J. Org. Chem., 59 (1994) 7959; J.S. Carey and E.J. Thomas, Tetrahedron Lett., (1993) 3935; J.A. Marshall and Y.J. Tang, J. Org. Chem., 58 (1993) 3233; Y. Yamamoto, K. Kobayashi, H. Ohano and I.J. Katoda, J. Org. Chem., 57 (1992) 7003; M. Benechie and F. Khuong-Huu, Synlett, (1992) 266; A. Bernardi, G. Poli, C. Scolastico and M. Zanda, J. Org. Chem., 56 (1991) 6961; J.A. Marshall and D.V. Yashunsky, J. Org. Chem., 56 (1991) 5493; J.M. Chong and E.K. Mar, Tetrahedron, (1989) 7709.
14. [6] W.C. Still and C. Sreekumar, J. Am. Chem. Soc., 106 (1980) 1201.
15. [7] E.J. Corey and B. De, J. Am. Chem. Soc., 106 (1984) 2735; P.C.M. Chan and J.M. Chong, J. Org. Chem., 57 (1988) 1242.
16. [7] E.J. Corey and B. De, J. Am. Chem. Soc., 106 (1984) 2735; P.C.M. Chan and J.M. Chong, J. Org. Chem., 57 (1988) 1242.
17. [8] J.A. Marshall and G.P. Luke, J. Org. Chem., 58 (1993) 6229; J.A. Marshall and X. Wang, J. Org. Chem., 57 (1992) 1242.
18. [8] J.A. Marshall and G.P. Luke, J. Org. Chem., 58 (1993) 6229; J.A. Marshall and X. Wang, J. Org. Chem., 57 (1992) 1242.
19. [9] F.R. Jensen and D.D. Davies, J. Am. Chem. Soc., 93 (1971) 4047; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 103 (1981) 5588; K.W. Lee and J.J. San Filippo, Organometallics, 1 (1982) 1496; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 104 (1982) 2831; G.F. Smith, H.G. Kuivila, R. Simon and L. Sultan, J. Am. Chem. Soc., 103 (1981) 833.
20. [9] F.R. Jensen and D.D. Davies, J. Am. Chem. Soc., 93 (1971) 4047; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 103 (1981) 5588; K.W. Lee and J.J. San Filippo, Organometallics, 1 (1982) 1496; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 104 (1982) 2831; G.F. Smith, H.G. Kuivila, R. Simon and L. Sultan, J. Am. Chem. Soc., 103 (1981) 833.
21. [9] F.R. Jensen and D.D. Davies, J. Am. Chem. Soc., 93 (1971) 4047; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 103 (1981) 5588; K.W. Lee and J.J. San Filippo, Organometallics, 1 (1982) 1496; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 104 (1982) 2831; G.F. Smith, H.G. Kuivila, R. Simon and L. Sultan, J. Am. Chem. Soc., 103 (1981) 833.
22. [9] F.R. Jensen and D.D. Davies, J. Am. Chem. Soc., 93 (1971) 4047; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 103 (1981) 5588; K.W. Lee and J.J. San Filippo, Organometallics, 1 (1982) 1496; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 104 (1982) 2831; G.F. Smith, H.G. Kuivila, R. Simon and L. Sultan, J. Am. Chem. Soc., 103 (1981) 833.
23. [9] F.R. Jensen and D.D. Davies, J. Am. Chem. Soc., 93 (1971) 4047; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 103 (1981) 5588; K.W. Lee and J.J. San Filippo, Organometallics, 1 (1982) 1496; J.J. San Filippo and J. Silbermann, J. Am. Chem. Soc., 104 (1982) 2831; G.F. Smith, H.G. Kuivila, R. Simon and L. Sultan, J. Am. Chem. Soc., 103 (1981) 833.
24. [10] M. Tanaka and I. Ogata, Bull. Chem. Soc. Jpn., 48 (1975) 1094.
25. [11] H. Schumann and B.C. Wassermann, J. Organomet. Chem., 365 (1989) C1; H. Schumann, B.C. Wassermann and F.E. Hahn, Organometallics, 11 (1992) 2803; H. Schumann, B.C. Wassermann and J. Pickardt, Organometallics, 12 (1993) 2803; J.C. Podesta and G.E. Radivoy, Organometallics, 13 (1994) 3364; J.C. Podesta, A.B. Chopa, G.E. Radivoy and C.A. Vitale, J. Organomet. Chem., 494 (1995) 11.
26. [11] H. Schumann and B.C. Wassermann, J. Organomet. Chem., 365 (1989) C1; H. Schumann, B.C. Wassermann and F.E. Hahn, Organometallics, 11 (1992) 2803; H. Schumann, B.C. Wassermann and J. Pickardt, Organometallics, 12 (1993) 2803; J.C. Podesta and G.E. Radivoy, Organometallics, 13 (1994) 3364; J.C. Podesta, A.B. Chopa, G.E. Radivoy and C.A. Vitale, J. Organomet. Chem., 494 (1995) 11.
27. [11] H. Schumann and B.C. Wassermann, J. Organomet. Chem., 365 (1989) C1; H. Schumann, B.C. Wassermann and F.E. Hahn, Organometallics, 11 (1992) 2803; H. Schumann, B.C. Wassermann and J. Pickardt, Organometallics, 12 (1993) 2803; J.C. Podesta and G.E. Radivoy, Organometallics, 13 (1994) 3364; J.C. Podesta, A.B. Chopa, G.E. Radivoy and C.A. Vitale, J. Organomet. Chem., 494 (1995) 11.
28. [11] H. Schumann and B.C. Wassermann, J. Organomet. Chem., 365 (1989) C1; H. Schumann, B.C. Wassermann and F.E. Hahn, Organometallics, 11 (1992) 2803; H. Schumann, B.C. Wassermann and J. Pickardt, Organometallics, 12 (1993) 2803; J.C. Podesta and G.E. Radivoy, Organometallics, 13 (1994) 3364; J.C. Podesta, A.B. Chopa, G.E. Radivoy and C.A. Vitale, J. Organomet. Chem., 494 (1995) 11.
29. [11] H. Schumann and B.C. Wassermann, J. Organomet. Chem., 365 (1989) C1; H. Schumann, B.C. Wassermann and F.E. Hahn, Organometallics, 11 (1992) 2803; H. Schumann, B.C. Wassermann and J. Pickardt, Organometallics, 12 (1993) 2803; J.C. Podesta and G.E. Radivoy, Organometallics, 13 (1994) 3364; J.C. Podesta, A.B. Chopa, G.E. Radivoy and C.A. Vitale, J. Organomet. Chem., 494 (1995) 11.
30. [12] J. Otera, Y. Yosshinaga, T. Yamaji, T. Yoshioka and Y. Kawasaki, Organometallics, 4 (1985) 1213.
31. [13] M.F. Connil, B. Jousseaume, N. Noiret and M. Pereyre, Organometallics, 13 (1994) 24.
32. [14] D. Doddrell, I. Burfitt, W. Kitching, M. Bullpit, C.-H. Lee, R.J. Mynott, J.L. Considine, H.G. Kuivila and R.H. Sarma, J. Am. Chem. Soc., 96 (1974) 1640.
33. [15] T.P. Lockhart and W.F. Manders, J. Am. Chem. Soc., 109 (1987) 7015.
34. [16] H. Schumann and Schumann, in U. Krüerker (ed.), Gmelin Handbook of Inorganic Chemistry, Vol. 1(5), Springer, Berlin, 1976, pp. 93-120.
35. [17] A.J. Streitwieser, T.D. Walsh and J.R.J. Wolfe, J. Am. Chem. Soc., 87 (1965) 3682.
36. [18] J. Kenyon, Org. Synth., 6 (1926) 68.
37. [19] A. Rahm, Thesis, Bordeaux, 1976.
38. [20] J. Klein, S. Neels and R. Borsdorf, J. Chem. Soc., Perkin Trans. 2, (1994) 2523.
39. [21] J.K. Kochi, Organometallic Mechanisms and Catalysis, Academic Press, New York, 1978, p. 500.
40. [22] M.A. Cordonnier, Ph.D. Thesis, Lyon I, 1994.
41. [23] K. Hayashi, J. Iyoda and I. Shiihara, J. Organomet. Chem., 10 (1967) 81.