Chiral Lewis acid catalysis in radical reactions: Enantioselective conjugate radical additions

Journal of the American Chemical Society

Volumn 118, Issue 38, 1996, Pages 9200-9201

  Sibi, Mukund P ^a   Ji, Jianguo ^a   Wu, Jason Hongliu ^b   Gürtler, Stephan ^b   Porter, Ned A ^b  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029804421     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9623929     Document Type: Article

References (27)

1. (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. (a) Evans, D. A.; Murray, J. A.; Matt, P. v.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
4. (b) Evans, D. A.; Miller, S. J.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460.
5. (c) Corey, E. J.; Imai, N.; Zhang, H-Y. J. Am. Chem. Soc. 1991, 113, 728.
6. (a) Urabe, H.; Yamashita, K.; Suzuki, K.; Kobayashi, K.; Sato, F. J. Org. Chem. 1995, 60, 3576.
7. (b) Murakata, M.; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481.
8. Wu, J. H.; Radinov, R.; Porter, N. A. J. Am. Chem. Soc. 1995, 117, 11029.
9. For discussion on acyclic diastereoselection in radical reactions, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (c) Smadja, W. Synlett 1994, 1. For early work on conjugate radical addition, see: (d) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
10. For discussion on acyclic diastereoselection in radical reactions, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (c) Smadja, W. Synlett 1994, 1. For early work on conjugate radical addition, see: (d) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
11. For discussion on acyclic diastereoselection in radical reactions, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (c) Smadja, W. Synlett 1994, 1. For early work on conjugate radical addition, see: (d) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
12. For discussion on acyclic diastereoselection in radical reactions, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995. (b) Porter, N. A.; Giese, B.; Curran, D. P. Acc. Chem. Res. 1991, 24, 296. (c) Smadja, W. Synlett 1994, 1. For early work on conjugate radical addition, see: (d) Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007.
13. Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779 and references cited therein.
14. For selected recent examples on the use of Lewis acids in radical reactions, see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (h) Feldman, K. S.; Romaneli. A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
15. For selected recent examples on the use of Lewis acids in radical reactions, see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (h) Feldman, K. S.; Romaneli. A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
16. For selected recent examples on the use of Lewis acids in radical reactions, see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (h) Feldman, K. S.; Romaneli. A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
17. For selected recent examples on the use of Lewis acids in radical reactions, see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (h) Feldman, K. S.; Romaneli. A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
18. For selected recent examples on the use of Lewis acids in radical reactions, see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (h) Feldman, K. S.; Romaneli. A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
19. For selected recent examples on the use of Lewis acids in radical reactions, see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (h) Feldman, K. S.; Romaneli. A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
20. For selected recent examples on the use of Lewis acids in radical reactions, see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (h) Feldman, K. S.; Romaneli. A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
21. For selected recent examples on the use of Lewis acids in radical reactions, see: (a) Renaud, P.; Gerster, M. J. Am. Chem. Soc. 1995, 117, 6607. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259. (c) Renaud, P.; Moufid, N.; Kuo, L. H.; Curran, D. P. J. Org. Chem. 1994, 59, 3547. Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guerrin, B.; Chabot, C.; Mackintosh, N.; Ogilve, W. W. Synlett 1995, 449. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Newcomb, M.; Ha, C. Tetrahedron Lett. 1991, 32, 6493. (h) Feldman, K. S.; Romaneli. A. L.; Ruckle, R. E., Jr.; Jean, G. J. Org. Chem. 1992, 57, 100.
22. The starting materials 5 and 8 and the ligands were prepared using literature procedures.
23. Bisoxazolines have been used as a ligand for a variety of reactions. For a review, see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339.
24. 2, rare earth triflates) were also evaluated in the conjugate radical addition with limited success or with no improvement over 6a-c.
25. Chapuis, C.; Jurczak, J. Helv. Chim. Acta 1987, 70, 436.
26. Four-coordinate planar, five-coordinate square pyramidal, or octahedral with axial counterions, shown as structure 10, can provide "planar" equivalent complexes of substrate and ligand.
27. Four-coordinate tetrahedral, five-coordinate square pyramidal or trigonal bipyramidal (shown as structure 11), or octahedral with counterions adopting a cis arrangement all can provide "tetrahedral" equivalent complexes of substrate and ligand. For the octahedral complex, the counterions adopt one of the two possible axial-equatorial arrangements due to steric constraints. Support for this model comes from Corey's work on Diels-Alder cycloadditions (ref 2c). Also see: Desimoni, G.; Faita, G.; Righetti, P. P. Tetrahedron Lett. 1996, 37, 3027.