NMR study on ligand exchange reaction between a chiral allylsilane and SnCl4

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1335-1338

  Dias, Luiz C ^a   Meira, Paulo R R ^a   Ferreira, Edílson ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000650089     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990869q     Document Type: Article

References (27)

1. (a) Dias, L. C.; Giacomini, R. J. Braz. Chem. Soc. 1998, 9, 357.
2. (b) Dias, L. C.; Giacomini, R. Tetrahedron Lett. 1998, 39, 5343.
3. (c) Dias, L. C.; Meira, P. R. R. Synlett, in press.
4. (d) See also: Evans, D. A.; Coleman, P. J.; Dias, L. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2737.
5. (a) Boaretto, A.; Marton, D.; Tagliavini, G.; Ganis, P. J. Organomet. Chem. 1987, 321, 199.
6. (b) Tagliavini, G. Rev. Silicon, Germanium, Tin Lead Cmpd. 1985, 8, 237.
7. Keck, G. E.; Abbot, D. E. Tetrahedron Lett. 1984, 25, 1883.
8. (b) Keck, G. E. and Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847.
9. (c) See also: Keck, G. E.; Castellino, S.; Andrus, M. B. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed.: NATO ASI Series C; Kluwer Academic: Dordrecht, 1989; Vol. 289, Chapter 5, pp 73-105.
10. Yamamoto, Y.; Maeda, N.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1983, 742.
11. (a) Denmark, S. E.; Wilson, T.; Willson, T. M. J. Am. Chem. Soc. 1988, 110, 984.
12. (b) Denmark, S. E.; Weber, E. J.; Wilson, T.; Willson, T. M. Tetrahedron 1989, 45, 1053.
13. (c) Denmark, S. E.; Almstead, N. G. Tetrahedron 1992, 48, 5565.
14. (d) Denmark, S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133.
15. Naruta, Y.; Nishigaishi, Y.; Maruyama, K. Tetrahedron 1989, 45, 1067.
16. 4 even at room temperature. See also ref 5c.
17. 4.
18. (a) Almendras, P.; Gruttadauria, M.; Helliwell, M.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1997, 2549.
19. (b) Almendras, P.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1997, 2561.
20. (c) Thomas, E. J. Chem. Commun. 1997, 411.
21. For papers dealing with coordination of heteroelements to electron-defficient tin, see: (a) Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046.
22. (b) Ochiai, M.; Iwaki, S.; Nagao, Y.; Kitagawa, S.; Munakat, M. Tetrahedron Lett. 1991, 32, 4945.
23. (c) Brown, J. M.; Pearson, M.; Jastrzebski, J. T. B. H.; Koten, G. V. J. Chem. Soc., Chem. Commun. 1992, 1440.
24. 4 compared to allylsilane 1 (1.0 equiv, 0.15 M solution) under the same conditions led to about 50% conversion, and the resulting NMR spectrum did not change with time.
25. Sn-H = 78 Hz).
26. 1H NMR spectrum at -60°C is due to the fact that this experiment has been done in a 10 mm NMR resonance tube.
27. Chemical shifts in ppm (multiplicity) for the olefinic hydrogens: allylsilane 4, 4.73 (sl), 4.79 (d), 5.78 (m); allylstannane 5, 5.33 (d), 5.40 (d), 5.97 (m); allylsilane 6, 4.62 (s), 4.67 (s); allylstannane 7, 5.15, 5.22.