On the relative reactivities of allyl, crotyl, α-oxygenated crotyl, γ-oxygenated α-methylallyl, and allenyl tri-n-butylstannane reagents in Lewis acid promoted additions to aldehydes

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2904-2907

  Marshall, James A ^a   Jablonowski, Jill A ^a   Welmaker, Gregory S ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001091283     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9519975     Document Type: Article

References (26)

1. For an overview, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
2. Boron: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.1; pp 1-49.
3. Tin: ref 2 and Yamamoto, Y.; Sheda, N. Advances in Detailed Reaction Mechanisms; JAI Press, 1994: Vol. 3, pp 1-44.
4. (a) Marshall, J. A.; Tang, Y. Synlett 1992, 653.
5. (b) Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543 and references cited therein.
6. Marshall, J. A. Chemtracts: Org. Chem. 1992, 5, 75, Marshall, J. A, Chem. Rev. 1996, 96, 31.
7. Marshall, J. A. Chemtracts: Org. Chem. 1992, 5, 75, Marshall, J. A, Chem. Rev. 1996, 96, 31.
8. Marshall, J. A.; Perkins, J. F.; Wolf, M. A. J. Org. Chem. 1995, 60, 5556.
9. Kinetics have been reported for reactions of allylic silanes, stannanes, and germanes with carbocations. Hagen, G.; Mayr, H. J. Am. Chem. Soc. 1991, 113, 4954.
10. These studies were initiated at the University of South Carolina. Preliminary results are reported in the Ph.D. Thesis of G. S. Welmaker, University of South Carolina, 1992.
11. For leading references to the synthesis of these stannanes, see: Marshall, J, A.; Jablonowski, J. A.; Elliott, L. M. J. Org. Chem. 1995, 60, 2662.
12. Keck and co-workers have also noted that trans-crotyl tri-n-butylstannane is more reactive than the cis isomer in additions to various aldehydes. Keck, G. E.; Savin, K, A.; Cressman, E. N. K.; Abbott, D. E. J. Org. Chem. 1994, 53, 7889.
13. Marshall, J. A.; Welmaker, G. S.; Gung, B. W. J. Am. Chem. Soc. 1991, 113, 647.
14. Marshall, J. A.; Welmaker, G. S. Tetrahedron Lett 1991, 32, 2101.
15. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
16. Cf. Marshall, J. A.; Gung, W. Y, Tetrahedron 1989, 45, 1043. Marshall, J. A.; Gung, B. W. Israel J. Chem. 1991, 31, 199. Marshall, J. A.; Yashunsky, D. V. J. Org. Chem. 1991, 56, 5493.
17. Cf. Marshall, J. A.; Gung, W. Y, Tetrahedron 1989, 45, 1043. Marshall, J. A.; Gung, B. W. Israel J. Chem. 1991, 31, 199. Marshall, J. A.; Yashunsky, D. V. J. Org. Chem. 1991, 56, 5493.
18. Cf. Marshall, J. A.; Gung, W. Y, Tetrahedron 1989, 45, 1043. Marshall, J. A.; Gung, B. W. Israel J. Chem. 1991, 31, 199. Marshall, J. A.; Yashunsky, D. V. J. Org. Chem. 1991, 56, 5493.
19. 3SnLi. Matarasso-Tchiroukhine, E.; Cadiot, P. J. Organomet. Chem. 1976, 121, 155, 169.
20. Marshall, J. A.; Jablonowski, J. A.; Luke, G. P. J. Org. Chem. 1994, 59, 7825.
21. Cf. Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958. Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639. Henry, K J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817.
22. Cf. Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958. Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639. Henry, K J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817.
23. Cf. Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958. Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639. Henry, K J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817.
24. Cf. Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958. Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. Aspinall, H. C.; Browning, A. F.; Greeves, N.; Ravenscroft, P. Tetrahedron Lett. 1994, 35, 4639. Henry, K J.; Grieco, P. A.; Jagoe, C. T. Tetrahedron Lett. 1992, 33, 1817.
25. 3.
26. Marshall, J. A.; Xie, S. J. Org. Chem. 1995, 60, 7230.