Enantioselective radical reactions: The use of metal triflimides as Lewis acids

Tetrahedron Asymmetry

Volumn 14, Issue 19, 2003, Pages 2879-2882

  Sibi, Mukund P ^a   Petrovic, Goran ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDE; IRON DERIVATIVE; LEWIS ACID; LIGAND; MAGNESIUM DERIVATIVE; METAL; OXAZOLINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; EVALUATION; PRIORITY JOURNAL; RADICAL REACTION; REACTION ANALYSIS;

EID: 0348169273     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00543-3     Document Type: Article

References (33)

1. For recent monographs, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999.
2. For recent monographs, see: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000; (b) Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: New York, 1999.
3. Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1 & 2.
4. Sibi M. P., Rheault T. R. Renaud P., Sibi M. P. Radicals in Organic Synthesis. 1:2001;461-478 Wiley-VCH, Weinheim.
5. Sibi M. P., Porter N. A. Acc. Chem. Res. 32:1999;163-171.
6. Renaud P., Gèrster M. Angew. Chem., Int. Ed. Engl. 37:1998;2563-2579.
7. For selected examples, see: (a) Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201; (b) Sibi, M. P.; Ji, J. G. J. Org. Chem. 1997, 62, 3800-3801; (c) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417-2428; (d) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299-302; (e) Sibi, M. P.; Shay, J. J.; Ji, J. G. Tetrahedron Lett. 1997, 38, 5955-5958; (f) Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929-2932; (g) Yang, D.; Gu, S.; Yan, Y. L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612-8613.
8. For selected examples, see: (a) Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201; (b) Sibi, M. P.; Ji, J. G. J. Org. Chem. 1997, 62, 3800-3801; (c) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417-2428; (d) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299-302; (e) Sibi, M. P.; Shay, J. J.; Ji, J. G. Tetrahedron Lett. 1997, 38, 5955-5958; (f) Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929-2932; (g) Yang, D.; Gu, S.; Yan, Y. L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612-8613.
9. For selected examples, see: (a) Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201; (b) Sibi, M. P.; Ji, J. G. J. Org. Chem. 1997, 62, 3800-3801; (c) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417-2428; (d) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299-302; (e) Sibi, M. P.; Shay, J. J.; Ji, J. G. Tetrahedron Lett. 1997, 38, 5955-5958; (f) Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929-2932; (g) Yang, D.; Gu, S.; Yan, Y. L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612-8613.
10. For selected examples, see: (a) Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201; (b) Sibi, M. P.; Ji, J. G. J. Org. Chem. 1997, 62, 3800-3801; (c) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417-2428; (d) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299-302; (e) Sibi, M. P.; Shay, J. J.; Ji, J. G. Tetrahedron Lett. 1997, 38, 5955-5958; (f) Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929-2932; (g) Yang, D.; Gu, S.; Yan, Y. L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612-8613.
11. For selected examples, see: (a) Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201; (b) Sibi, M. P.; Ji, J. G. J. Org. Chem. 1997, 62, 3800-3801; (c) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417-2428; (d) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299-302; (e) Sibi, M. P.; Shay, J. J.; Ji, J. G. Tetrahedron Lett. 1997, 38, 5955-5958; (f) Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929-2932; (g) Yang, D.; Gu, S.; Yan, Y. L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612-8613.
12. For selected examples, see: (a) Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201; (b) Sibi, M. P.; Ji, J. G. J. Org. Chem. 1997, 62, 3800-3801; (c) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417-2428; (d) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299-302; (e) Sibi, M. P.; Shay, J. J.; Ji, J. G. Tetrahedron Lett. 1997, 38, 5955-5958; (f) Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929-2932; (g) Yang, D.; Gu, S.; Yan, Y. L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612-8613.
13. For selected examples, see: (a) Sibi, M. P.; Ji, J. G.; Wu, J. H.; Gürtler, S.; Porter, N. A. J. Am. Chem. Soc. 1996, 118, 9200-9201; (b) Sibi, M. P.; Ji, J. G. J. Org. Chem. 1997, 62, 3800-3801; (c) Iserloh, U.; Curran, D. P.; Kanemasa, S. Tetrahedron: Asymmetry 1999, 10, 2417-2428; (d) Murakata, M.; Tsutsui, H.; Hoshino, O. Org. Lett. 2001, 3, 299-302; (e) Sibi, M. P.; Shay, J. J.; Ji, J. G. Tetrahedron Lett. 1997, 38, 5955-5958; (f) Sibi, M. P.; Manyem, S. Org. Lett. 2002, 4, 2929-2932; (g) Yang, D.; Gu, S.; Yan, Y. L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612-8613.
14. 4: C, 7.80; N, 4.55. Found: C, 7.37; N, 4.71. Zinc(II) bis-triflimide. Zinc powder (0.23 g, 3.52 mmol) was added to a solution of bistrifluoromethanesulfonimide (1.51 g, 5.39 mmol) in 9.0 mL of deionized water, and the resulting mixture was stirred at room temperature for 4 h. The mixture was filtered to remove excess zinc. The water was removed in vacuum and the crude was dried under vacuum at 150°C for 7 h to give 0.84 g (50%) of zinc(II) bis-triflimide.
15. 4: C, 7.80; N, 4.55. Found: C, 7.37; N, 4.71. Zinc(II) bis-triflimide. Zinc powder (0.23 g, 3.52 mmol) was added to a solution of bistrifluoromethanesulfonimide (1.51 g, 5.39 mmol) in 9.0 mL of deionized water, and the resulting mixture was stirred at room temperature for 4 h. The mixture was filtered to remove excess zinc. The water was removed in vacuum and the crude was dried under vacuum at 150°C for 7 h to give 0.84 g (50%) of zinc(II) bis-triflimide.
16. 4: C, 7.80; N, 4.55. Found: C, 7.37; N, 4.71. Zinc(II) bis-triflimide. Zinc powder (0.23 g, 3.52 mmol) was added to a solution of bistrifluoromethanesulfonimide (1.51 g, 5.39 mmol) in 9.0 mL of deionized water, and the resulting mixture was stirred at room temperature for 4 h. The mixture was filtered to remove excess zinc. The water was removed in vacuum and the crude was dried under vacuum at 150°C for 7 h to give 0.84 g (50%) of zinc(II) bis-triflimide.
17. For the use of silyl triflimides in enantioselective Diels-Alder reaction, see: Mathieu B., de Fays L., Ghosez L. Tetrahedron Lett. 41:2000;9561-9564.
18. For a comparison of lithium triflimide with lithium perchlorate, see: Handy S. T.:, Grieco P. A., Mineur C., Ghosez L. Synlett. 1995;565-567.
19. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
20. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
21. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
22. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
23. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
24. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
25. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
26. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
27. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
28. For the use of metal triflimides as Lewis acids, see: (a) Grieco, P. A.; Handy, S. T. Tetrahedron Lett. 1997, 38, 2645-2648; (b) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2000, 80-82; (c) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Chem. Commun. 2002, 1564-1565; (d) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839-841; (e) Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265-266; (f) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H.; Maruta, M. Synlett 1996, 171-172; (g) Ishihara, K.; Hiraiwa, Y.; Yamamoto, H. Synlett 2001, 1851-1854; (h) Mathieu, B.; Ghosez, L. Tetrahedron 2002, 58, 8219-8226; (i) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J.-R. Synthesis 2002, 2211-2214; (j) Tamion, R.; Mineur, C.; Ghosez, L. Tetrahedron Lett. 1995, 36, 8977-8980.
29. For a recent review, see: Sibi M. P., Manyem S. Tetrahedron. 56:2000;8033-8061.
30. t 25.1 min (R-isomer)].
31. For a review on bisoxazolines, see: Ghosh A. K., Mathivannan P., Cappiello J. Tetrahedron: Asymmetry. 9:1998;1-45.
32. Starting materials 1, 6, 8, products 2, 7, 9, and ligands 3, 4, 5, 10, 11 are known compounds. See: Refs 4a, b, c, e and 13 for information. Product 7 showed spectral characteristics consistent with its structure.
33. Sibi, M. P.; Zhang, R.; Manyem, S. J. Am. Chem. Soc. 2003, 125, in press.