Mechanistic studies on selectivity in the B(C6F5)3-catalyzed allylstannation of aldehydes: Is hypercoordination at boron responsible?

Organic Letters

Volumn 2, Issue 5, 2000, Pages 695-698

  Blackwell, James M ^a   Piers, Warren E ^a   Parvez, Masood ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001740668     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0000105     Document Type: Article

References (37)

1. Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, 1995; p 91.
2. (a) Ooi, T.; Uraguchi, D.; Kagushima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327.
3. (b) Maruoka, K.; Ooi, T. Chem. Eur. J. 1999, 5, 829.
4. (c) Ooi, T.; Uraguchi, D.; Maruoka, K. Tetrahedron Lett. 1998, 39, 8105.
5. (a) Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 345.
6. (b) Ishihara, K.; Yamamoto, H. Eur. J. Org. Chem. 1999, 527.
7. Akiba, K. The Chemistry of Hypervalent Compounds; John Wiley & Sons: Chichester, 1999.
8. (a) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
9. (b) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.
10. (a) Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265.
11. (b) Suzuki, I.; Yamamoto, Y. J. Org. Chem. 1993, 58, 4783.
12. (c) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
13. See ref 1, pp 134-146 and references therein.
14. Lee, D. Y.; Martin, J. C. J. Am. Chem. Soc. 1984, 106, 5745.
15. For the Lewis acids with larger central atoms in Maruoka's studies, the hypercoordinate explanation is more reasonable.
16. (a) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440.
17. (b) Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. Submitted for publication.
18. (c) See also: Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem. 1999, 64, 4887.
19. Parks, D. J.; Piers, W. E.; Parvez, M.; Atencio, R.; Zaworotko, M. J. Organometallics 1998, 17, 1369.
20. 4 groups, attesting to the steric impact of this Lewis acid.
21. Lambert, J. B.; Zhao, Y.; Wu, H.; Tse, W. C.; Kuhlmann, B. J. Am. Chem. Soc. 1999, 121, 5001.
22. Kidd, R. G. In NMR of Newly Accessible Nuclei, Volume 2; Laszlo, P., Ed.; Academic Press: New York, 1983.
23. 5-substituted boranes. (a) Horton, A. D.; de With, J. Organometallics 1997, 16, 5424.
24. Lambert, J. B.; Zhao, Y.; Wu, H. J. Org. Chem. 1999, 64, 2729.
25. 3 leads to partial allylation which also complicates analysis.
26. 1H NMR at low temperature.
27. (a) Davies, A. G.; Goddard, J. P.; Hursthouse, M. B.; Walker, N. P. C. J. Chem. Soc., Dalton Trans. 1986, 1873.
28. (b) Edlund, U.; Arshadi, M.; Johnels, D. J. Organomet. Chem. 1993, 456, 57.
29. (c) Blaschette, A.; Wieland, E.; Jones, P. G.; Hippel, I. J. Organomet. Chem. 1993, 445, 55.
30. (d) Nugent, W. A.; McKinney, R. J.; Harlow, R. L. Organometallics 1984, 3, 1315.
31. Chelation of similar substrates to neutral tin Lewis acids is also precedented: (a) Keck, G. E.; Andrus, M. B.; Castellino, S. J. Am. Chem. Soc. 1989, 111, 8136.
32. (b) Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847.
33. (c) Reetz, M. T.; Harms, K.; Reif, W. Tetrahedron Lett. 1988, 29, 5881.
34. (d) Wong, C. Y.; Woolins, J. D. Coord. Chem. Rev. 1994, 130, 175.
35. 19F NMR experiments pertaining to these experiments: (a) Figure S1.
36. (b) Figures S2.
37. Yamataka, H. Nishikawa, K.; Hanafusa, T. Chem. Lett. 1990, 1711.