Planar chiral C2-symmetric bisferrocenes: Stereoselective pinacol coupling of α-substituted ferrocenecarboxaldehydes

Tetrahedron Letters

Volumn 39, Issue 30, 1998, Pages 5385-5388

  Taniguchi, Nobukazu ^a   Uemura, Motokazu ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

1,2 diols; Ferrocenes; Inversion; Nucleophilic substitution; Pinacol coupling; Planar chirality

Indexed keywords

FERROCENE DERIVATIVE; FERROCENECARBOXALDEHYDE; SAMARIUM; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032560830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01080-6     Document Type: Article

References (22)

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2. 1 Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547. Becker, H.; King, S. B.; Taniguchi, M.; Vanhessche, K. P. M.; Sharpless, K. B. J. Org. Chem. 1995, 60, 3940-3941 and references cited therein.
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4. 2 For reviews; Molander, G. A. Chem. Rev. 1992, 92, 29-68. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. Sonderquist, J. A. Aldrichimica Acta 1991, 24, 15-23.
5. 2 For reviews; Molander, G. A. Chem. Rev. 1992, 92, 29-68. Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307-338. Sonderquist, J. A. Aldrichimica Acta 1991, 24, 15-23.
6. 3 Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089. Taniguchi, N.; Uemura, M. Synlett 1997, 51-53.
7. 3 Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088-6089. Taniguchi, N.; Uemura, M. Synlett 1997, 51-53.
8. 3): δ for 2 (R = Me); 1.32 (6H, s), 2.66 (2H, br), 3.77-3.97 (4H, m), 4.07 (10H, s), 4.20-4.21 (2H, m), 4.24 (2H, s). for 3 (R = Me); 2.10 (6H, s), 2.24 (2H, br), 3.99-4.07 (6H, m), 4.14 (10H, s), 4.21 (2H, s). for 4 (R = Me); 1.69 (3H, s), 1.77 (3H, s), 2.38 (2H, br), 3.99-4.07 (6H, m), 4.10 (5H, s), 4.11 (5H, s), 4.44 (2H, br).
9. 5 Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733-6745.
10. 6 Taudien, S.; Riant, O.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 3513-3516, Gockel, G.; Hoffmann, P.; Kleimann, H.; Klusacek, H.; Marquarding, D.; Ugi, I. Tetrahedron Lett. 1970, 21, 1771-1774.
11. 6 Taudien, S.; Riant, O.; Kagan, H. B. Tetrahedron Lett. 1995, 36, 3513-3516, Gockel, G.; Hoffmann, P.; Kleimann, H.; Klusacek, H.; Marquarding, D.; Ugi, I. Tetrahedron Lett. 1970, 21, 1771-1774.
12. 7 An addition of MeLi to the α-diphenylphosphino ferrocenecarboxaldehyde gave predominantly one diastereomer via probably anti-carbonyl conformation. Therefore, even with the α-diphenylphosphino substituent, samarium metal would attack the anti-carbonyl, giving ketyl radical intermediate 6.
13. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
14. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
15. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
16. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
17. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
18. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
19. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
20. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
21. 8 A review; Togni, A.; Hayashi, T. (Eds) Ferrocenes; VCH: New York, Weinheim, 1995. Some representative references; Gokel, G. W.; Ugi, I. K. Angew. Chem. Int. Ed. Engl. 1971, 10, 191. Marquarding, D.; Klusacek, H.; Gokel, G. W.; Hoffman, P.; Ugi, I. K. J. Am. Chem. Soc. 1970, 92, 5389-5393. Gokel, G. W.; Marquarding, D.; Ugi, I. K. J. Org. Chem. 1972, 37, 3052-3058. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, M.; Hamada, Y.; Matsumoto, A., Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138-1151. Locke, A. J., Gouti, N.; Richards, C. J.; Hibbs, D. E.; Hursthous, M. B.; Tetrahedron 1996, 52, 1461-1472. Perea, J. J. A.; Ireland, T.; Knochel, P.; Tetrahedron Lett. 1997, 38, 5961-5964. Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062-4066. Sawamura, M.; Hamashita, H.; Sugawara, M.; Kuwano, R.; Ito, Y. Organometallics 1995, 14, 4549-4558.
22. N1 reaction was largely dependent on the substrate, nucleophile and reaction conditions.