Enantioselective Free Radical Allyl Transfers from Allylsilanes Promoted by Chiral Lewis Acids

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6702-6703

  Porter, Ned A ^a   Wu, Jason Hongliu ^a   Zhang, Guiru ^a   Reed, Aimee D ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001750953     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971199+     Document Type: Article

References (30)

1. (a) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296.
2. (b) Smadja, W. Synlett 1994, 1.
3. (c) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995.
4. (a) Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
5. (b) Sibi, M. P.; Ji, J.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200.
6. (c) Nanni, D.; Curran, D. P. Tetrahedron: Asymmetry 1996, 8, 2417.
7. (d) Blumenstein, M.; Schwarzkopf, K.; Metzger, J. O. Angew. Chem, 1997, 36, 235.
8. (a) Guindon, Y.; Guerin, B.; Chabot, C.; Ogilvie, W. J. Am. Chem. Soc. 1996, 118, 12528.
9. (b) Guindon, Y.; Guerin, B.; Rancourt, J.; Chabot, C.; Mackintosh, N.; Ogilvie, W. W. Pure Appl. Chem. 1996, 68, 89.
10. (c) Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Curran, D. P. Tetrahedron Lett. 1996, 37, 6387.
11. (a) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779.
12. (b) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607.
13. (c) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259.
14. (d) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547.
15. (e) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464.
16. (f) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449.
17. (g) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945.
18. (h) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493.
19. (i) Feldman, K. S.; Romaneli, A. L.; Ruckle, R. E. Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
20. (j) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190.
21. (k) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Lett. 1997, 38, 2661.
22. (k) Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063. Lett. 1997, 38, 2661.
23. (a) Wu, J. H.; Zhang, G; Porter, N. A. Tetrahedron Lett. 1997, 38, 2067.
24. (b) Aluminum Lewis acids have also been used in similar transformations with modest selectivity: Fhal, A.-R.; Renaud, P. Tetrahedron Lett. 1997, 38, 2661.
25. The synthesis of this new bisoxazoline is reported in Supporting Information.
26. The fused indanylbisoxazoline that gives very high selectivity in reactions in which the Lewis acid is complexed to the radical trap gives very low selectivity in reactions such as eq 3 in which the Lewis acid is complexed to the radical in the stereodefining step. See: (a) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 6800.
27. The fused indanylbisoxazoline that gives very high selectivity in reactions in which the Lewis acid is complexed to the radical trap gives very low selectivity in reactions such as eq 3 in which the Lewis acid is complexed to the radical in the stereodefining step. See: (a) Davies, I. W.; Gerena, L.; Castonguay, L.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Chem. Soc., Chem. Commun. 1996, 1753. (b) Sibi, M. P.; Ji, J. J. Org. Chem. 1997, 62, 6800.
28. Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872.
29. Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229.
30. Tin Lewis acids have been shown to promote diastereoselective free radical transformations. See: Sibi, M. P.; Ji, J. G. J. Am. Chem. Soc. 1996, 118, 3063.