Practical and Efficient Enantioselective Conjugate Radical Additions

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3800-3801

  Sibi, Mukund P ^a   Ji, Jianguo ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000526974     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970558y     Document Type: Article

References (41)

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2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
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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.
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.
11. (d) For early work on conjugate radical addition see: Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. (e) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779 and references cited therein.
12. (d) For early work on conjugate radical addition see: Stack, J. G.; Curran, D. P.; Geib, S. V.; Rebek, J., Jr.; Ballester, P. J. Am. Chem. Soc. 1992, 114, 7007. (e) Sibi, M. P.; Jasperse, C. P.; Ji, J. J. Am. Chem. Soc. 1995, 117, 10779 and references cited therein.
13. Sibi, M. P.; Ji, J.; Wu, J. H.; Gurtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200.
14. Bisoxazolines have been used as a ligand for a variety of reactions. For a review see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. For leading references on selective aldol and Diels-Alder reactions with bisoxazolines see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814. Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481.
15. Bisoxazolines have been used as a ligand for a variety of reactions. For a review see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. For leading references on selective aldol and Diels-Alder reactions with bisoxazolines see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814. Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481.
16. Bisoxazolines have been used as a ligand for a variety of reactions. For a review see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. For leading references on selective aldol and Diels-Alder reactions with bisoxazolines see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814. Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481.
17. Bisoxazolines have been used as a ligand for a variety of reactions. For a review see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339. For leading references on selective aldol and Diels-Alder reactions with bisoxazolines see: Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798. Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814. Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481.
18. (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.
19. (b) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327.
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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
22. 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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
23. 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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
24. 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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
25. 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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
26. 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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
27. 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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
28. 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. (d) Toru, T.; Watanabe, Y.; Tsusaka, M.; Ueno, Y. J. Am. Chem. Soc. 1993, 115, 10464. (e) Guindon, Y.; Guérin, B.; Chabot, C.; Ogilvie, W. W. J. Am. Chem. Soc. 1996, 118, 12528. (f) Andrus, M. B.; Argade, A. B.; Chen, X.; Pamment, M. G. Tetrahedron Lett. 1995, 36, 2945. (g) Sibi, M. P.; Ji, J. J. Org. Chem. 1996, 61, 6090. (h) Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 190. (i) Nishida, M.; Ueyama, E.; Hayashi, H.; Ohtake, Y.; Yamaura, Y.; Yanaginuma, E.; Yonemitsu, O.; Nishida, A.; Kawahara, N. J. Am. Chem. Soc. 1994, 116, 6455.
29. The starting materials and the ligands were prepared using literature procedures. See the Supporting Information.
30. 2 dihedral angles for these ligands are 70°, 81°, and 10°, respectively.
31. The absolute stereochemistry of the product was established by hydrolysis to the known acid.
32. In structures A and B, the counterions are still within bonding distance from the metal. An extreme situation would be one in which the ions are completely dissociated, imparting a square planar geometry around the metal for A and a tetrahedral arrangement for B.
33. This organization is favored over the alternate cis-octahedral (tetrahedral) arrangement because it has the least amount of substrate: ligand and ligand:counterion steric interactions.
34. The substrate is in an s-cis conformation. This is based on our previous work (ref 4) and literature precedents: Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Am. Chem. Soc. 1995, 117, 4435. Chapuis, C.; Jurczak, J. Helv. Chim. Acta 1987, 70, 436.
35. The substrate is in an s-cis conformation. This is based on our previous work (ref 4) and literature precedents: Gothelf, K. V.; Hazell, R. G.; Jorgensen, K. A. J. Am. Chem. Soc. 1995, 117, 4435. Chapuis, C.; Jurczak, J. Helv. Chim. Acta 1987, 70, 436.
36. For work on octahedral cis-models using iron Lewis acids see: Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728.
37. For work on octahedral cis-models using titanium Lewis acids see: Johannsen, M.; Jorgensen, K. A. J. Org. Chem. 1995, 60, 5757; Haase, C.; Sarko, C. R.; DiMare, M. J. Org. Chem. 1995, 60, 1777; Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kuhnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
38. For work on octahedral cis-models using titanium Lewis acids see: Johannsen, M.; Jorgensen, K. A. J. Org. Chem. 1995, 60, 5757; Haase, C.; Sarko, C. R.; DiMare, M. J. Org. Chem. 1995, 60, 1777; Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kuhnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
39. For work on octahedral cis-models using titanium Lewis acids see: Johannsen, M.; Jorgensen, K. A. J. Org. Chem. 1995, 60, 5757; Haase, C.; Sarko, C. R.; DiMare, M. J. Org. Chem. 1995, 60, 1777; Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kuhnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
40. For an octahedral model using Mg Lewis acid see: Desimoni, G.; Faita, G.; Righetti, P. P. Tetrahedron Lett. 1996, 37, 3027
41. 2 and ligand 3f.