Mechanistic insights into perfluoroaryl borane-catalyzed allylstannations: Toward asymmetric induction with chiral boranes

Pure and Applied Chemistry

Volumn 76, Issue 3, 2004, Pages 615-623

  Morrison, D J ^a   Blackwell, J M ^a   Piers, W E ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; BORANE DERIVATIVE; CARBONYL DERIVATIVE; CATION; LEWIS ACID; PERFLUORO COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE; TIN;

ALLYLSTANNATION; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CONFERENCE PAPER; HYDROSILYLATION; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 2442461365     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200476030615     Document Type: Conference Paper

References (33)

1. 3: A.G. Massey and A. J. Park. J. Organomet. Chem. 2, 245-250 (1964); A. G. Massey and A. J. Park. J. Organomet. Chem. 5, 218-225 (1966).
2. 3: A.G. Massey and A. J. Park. J. Organomet. Chem. 2, 245-250 (1964); A. G. Massey and A. J. Park. J. Organomet. Chem. 5, 218-225 (1966).
3. E. Y.-X. Chen and T. J. Marks. Chem. Rev. 100, 1391-1434 (2000).
4. W. E. Piers and T. Chivers. Chem. Soc. Rev. 26, 345-354 (1997).
5. C. Bergquist, B. M. Bridgewater, C. J. Harlan, J. R. Norton, R. A. Friesner, G. Parkin. J. Am. Chem. Soc. 122, 10581-10590 (2000). See also: T. Beringhelli, D. Maggioni, G. D'Alfonso. Organometallics 20, 4927-4938 (2001).
6. C. Bergquist, B. M. Bridgewater, C. J. Harlan, J. R. Norton, R. A. Friesner, G. Parkin. J. Am. Chem. Soc. 122, 10581-10590 (2000). See also: T. Beringhelli, D. Maggioni, G. D'Alfonso. Organometallics 20, 4927-4938 (2001).
7. R. F. Childs, D. L. Mulholland, A. Nixon. Can. J. Chem. 60, 801-808 (1982).
8. Arylboron compounds as acid catalysts in organic synthesis: K. Ishihara and H. Yamamoto. Eur. J. Org. Chem. 527-538 (1999).
9. D. J. Parks and W. E. Piers. J. Am. Chem. Soc. 118, 9440-9441 (1996); D. J. Parks, J. M. Blackwell, W. E. Piers. J. Org. Chem. 65, 4887-4892 (1999).
10. D. J. Parks and W. E. Piers. J. Am. Chem. Soc. 118, 9440-9441 (1996); D. J. Parks, J. M. Blackwell, W. E. Piers. J. Org. Chem. 65, 4887-4892 (1999).
11. J. M. Blackwell, E. R. Sonmor, T. Scoccitti, W. E. Piers. Org. Lett. 2, 3921-3923 (2000).
12. D. J. Parks, W. E. Piers, M. Parvez, R. Atencio, M. J. Zaworotko. Organometallics 17 1369-1377 (1998).
13. J. M. Blackwell, W. E. Piers, M. Parvez, R. McDonald. Organometallic 21, 1400-1407 (2002).
14. J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers. J. Org. Chem. 64, 4887-4892 (1999); V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto. J. Org. Chem. 65, 6179-6186 (2000); V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto. Tetrahedron Lett. 40, 8919-8922 (1999); S. Chandrasekhar, C. R. Reddy, B. N. Babu. J. Org. Chem. 67, 9080-9082 (2002).
15. J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers. J. Org. Chem. 64, 4887-4892 (1999); V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto. J. Org. Chem. 65, 6179-6186 (2000); V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto. Tetrahedron Lett. 40, 8919-8922 (1999); S. Chandrasekhar, C. R. Reddy, B. N. Babu. J. Org. Chem. 67, 9080-9082 (2002).
16. J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers. J. Org. Chem. 64, 4887-4892 (1999); V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto. J. Org. Chem. 65, 6179-6186 (2000); V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto. Tetrahedron Lett. 40, 8919-8922 (1999); S. Chandrasekhar, C. R. Reddy, B. N. Babu. J. Org. Chem. 67, 9080-9082 (2002).
17. J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers. J. Org. Chem. 64, 4887-4892 (1999); V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto. J. Org. Chem. 65, 6179-6186 (2000); V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto. Tetrahedron Lett. 40, 8919-8922 (1999); S. Chandrasekhar, C. R. Reddy, B. N. Babu. J. Org. Chem. 67, 9080-9082 (2002).
18. J. M. Blackwell, D. J. Morrison, W. E. Piers. Tetrahedron 58, 8247-8254 (2002).
19. V. Gevorgyan, M. Rubin, J.-X. Liu, Y. Yamamoto. J. Org. Chem. 66, 1672-1675 (2001).
20. J.-M. Denis, H. Forintos, H. Szelke, G. Keglevich. Tetrahedron Lett. 43, 5569-5571 (2002).
21. M. Rubin and V. Gevorgyan. Org. Lett. 3, 2705-2707 (2001).
22. N. Asao, T. Ohishi, K. Sato, Y. Yamamoto. J. Am. Chem. Soc. 123, 6931-6932 (2001); N. Asao, T. Ohishi, K. Sato, Y. Yamamoto. Tetrahedron 58, 8195-8203 (2002).
23. N. Asao, T. Ohishi, K. Sato, Y. Yamamoto. J. Am. Chem. Soc. 123, 6931-6932 (2001); N. Asao, T. Ohishi, K. Sato, Y. Yamamoto. Tetrahedron 58, 8195-8203 (2002).
24. T. Ooi, D. Uraguchi, N. Kagoshima, K. Maruoka. J. Am. Chem. Soc. 120, 5327-5328 (1998).
25. K. Maruoka and T. Ooi. Chem. Eur. J. 5, 829-833 (1999).
26. J. M. Blackwell, W. E. Piers, R. McDonald. J. Am. Chem. Soc. 124, 1295-1306 (2002); J. M. Blackwell, W. E. Piers, M. Parvez. Org. Lett. 2, 695-698 (2000); see also: K. Gill and J. A. Marshall. J. Organomet. Chem. 624, 294-299 (2001).
27. J. M. Blackwell, W. E. Piers, R. McDonald. J. Am. Chem. Soc. 124, 1295-1306 (2002); J. M. Blackwell, W. E. Piers, M. Parvez. Org. Lett. 2, 695-698 (2000); see also: K. Gill and J. A. Marshall. J. Organomet. Chem. 624, 294-299 (2001).
28. J. M. Blackwell, W. E. Piers, R. McDonald. J. Am. Chem. Soc. 124, 1295-1306 (2002); J. M. Blackwell, W. E. Piers, M. Parvez. Org. Lett. 2, 695-698 (2000); see also: K. Gill and J. A. Marshall. J. Organomet. Chem. 624, 294-299 (2001).
29. S. E. Denmark and J. Fu. Chem. Rev. 103, 2763-2794 (2003).
30. D. J. Morrison and W. E. Piers. Org. Lett. 5, 2857-2860 (2003).
31. P. A. Deck, C. L. Beswick, T. J. Marks. J. Am. Chem. Soc. 120, 1772-1784 (1998).
32. The components of the equilibrium of Scheme 3 that are different than those of Scheme 2, i.e., IP and A, were prepared separately and their NMR spectroscopic signatures matched those observed in the equilibrium experiments.
33. D. J. Morrison and W. E. Piers. Unpublished results.