A new Ferrocene in the Asymmetric Addition of Diethylzinc to Aldehydes

Synlett

Volumn 1997, Issue 9, 1997, Pages 1051-1052

  Bolm, Carsten ^a   Muñiz Fernández, Kilian ^a   Seger, Andreas ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041685739     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1528     Document Type: Article

References (30)

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2. Reviews: Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Ed.; VCH Verlagsgesellschaft: Weinheim, 1995; p 105. Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475. Kagan, H. B.; Diter, P.; Gref, A.; Guillaneux, D.; Masson-Szymczak, A.; Rebière, F.; Riant, O.; Samuel, O.; Taudien, S. Pure Appl. Chem. 1996, 68, 29. Togni, A. Chimia 1996, 50, 86.
3. Reviews: Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Ed.; VCH Verlagsgesellschaft: Weinheim, 1995; p 105. Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475. Kagan, H. B.; Diter, P.; Gref, A.; Guillaneux, D.; Masson-Szymczak, A.; Rebière, F.; Riant, O.; Samuel, O.; Taudien, S. Pure Appl. Chem. 1996, 68, 29. Togni, A. Chimia 1996, 50, 86.
4. Reviews: Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Ed.; VCH Verlagsgesellschaft: Weinheim, 1995; p 105. Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475. Kagan, H. B.; Diter, P.; Gref, A.; Guillaneux, D.; Masson-Szymczak, A.; Rebière, F.; Riant, O.; Samuel, O.; Taudien, S. Pure Appl. Chem. 1996, 68, 29. Togni, A. Chimia 1996, 50, 86.
5. Reviews: Hayashi, T. In Ferrocenes; Togni, A., Hayashi, T., Ed.; VCH Verlagsgesellschaft: Weinheim, 1995; p 105. Togni, A. Angew. Chem. 1996, 108, 1581; Angew. Chem. Int. Ed. Engl. 1996, 35, 1475. Kagan, H. B.; Diter, P.; Gref, A.; Guillaneux, D.; Masson-Szymczak, A.; Rebière, F.; Riant, O.; Samuel, O.; Taudien, S. Pure Appl. Chem. 1996, 68, 29. Togni, A. Chimia 1996, 50, 86.
6. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. Richards, C. J., Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
7. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. Richards, C. J., Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
8. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. Richards, C. J., Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
9. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. Richards, C. J., Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
10. Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synlett 1995, 74. Nishibayashi, Y.; Uemura, S. Synlett 1995, 79. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10. Richards, C. J., Mulvaney, A. W. Tetrahedron: Asymmetry 1996, 7, 1419. Ahn, K. H.; Cho, C.-W.; Baek, H.-H.; Park, J.; Lee, S. J. Org. Chem. 1996, 61, 4937.
11. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometatlics 1995, 14, 5486. Nishibayashi, Y.; Segawa, K.; Takada, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
12. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometatlics 1995, 14, 5486. Nishibayashi, Y.; Segawa, K.; Takada, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
13. Richards, C. J.; Hibbs, D. E.; Hursthouse, M. B. Tetrahedron Lett. 1995, 36, 3745. Nishibayashi, Y.; Segawa, K.; Ohe, K.; Uemura, S. Organometatlics 1995, 14, 5486. Nishibayashi, Y.; Segawa, K.; Takada, H.; Ohe, K.; Uemura, S. Chem. Commun. 1996, 847.
14. Reviews: Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem. Int. Ed. Engl. 1991, 30, 49. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
15. Reviews: Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem. Int. Ed. Engl. 1991, 30, 49. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
16. Reviews: Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem. Int. Ed. Engl. 1991, 30, 49. Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833.
17. For our previous work on asymmetric dialkylzinc additions see: Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. 1990, 102, 206; Angew. Chem. Int. Ed. Engl. 1990, 29, 205. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. Bolm, C.; Müller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. Chem. Commun. 1993, 182. Bolm, C.; Müller, J. Tetrahedron 1994, 50, 4355. Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387.
18. For our previous work on asymmetric dialkylzinc additions see: Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. 1990, 102, 206; Angew. Chem. Int. Ed. Engl. 1990, 29, 205. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. Bolm, C.; Müller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. Chem. Commun. 1993, 182. Bolm, C.; Müller, J. Tetrahedron 1994, 50, 4355. Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387.
19. For our previous work on asymmetric dialkylzinc additions see: Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. 1990, 102, 206; Angew. Chem. Int. Ed. Engl. 1990, 29, 205. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. Bolm, C.; Müller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. Chem. Commun. 1993, 182. Bolm, C.; Müller, J. Tetrahedron 1994, 50, 4355. Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387.
20. For our previous work on asymmetric dialkylzinc additions see: Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. 1990, 102, 206; Angew. Chem. Int. Ed. Engl. 1990, 29, 205. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. Bolm, C.; Müller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. Chem. Commun. 1993, 182. Bolm, C.; Müller, J. Tetrahedron 1994, 50, 4355. Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387.
21. For our previous work on asymmetric dialkylzinc additions see: Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. 1990, 102, 206; Angew. Chem. Int. Ed. Engl. 1990, 29, 205. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. Bolm, C.; Müller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. Chem. Commun. 1993, 182. Bolm, C.; Müller, J. Tetrahedron 1994, 50, 4355. Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387.
22. For our previous work on asymmetric dialkylzinc additions see: Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. 1990, 102, 206; Angew. Chem. Int. Ed. Engl. 1990, 29, 205. Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191. Bolm, C.; Müller, J.; Schlingloff, G.; Zehnder, M.; Neuburger, M. Chem. Commun. 1993, 182. Bolm, C.; Müller, J. Tetrahedron 1994, 50, 4355. Bolm, C.; Derrien, N.; Seger, A. Synlett 1996, 387.
23. Other chiral ferrocenes in this reaction: Butsugan, Y.; Araki, S.; Watanabe, M. In Ferrocenes; Togni, A.; Hayashi, T., Ed.; VCH Verlagsgesellschaft: Weinheim, 1995; p 143. Wally, H.; Widholm, M.; Weissensteiner, W.; Schlögl, K. Tetrahedron: Asymmetry 1993, 4, 285.
24. Other chiral ferrocenes in this reaction: Butsugan, Y.; Araki, S.; Watanabe, M. In Ferrocenes; Togni, A.; Hayashi, T., Ed.; VCH Verlagsgesellschaft: Weinheim, 1995; p 143. Wally, H.; Widholm, M.; Weissensteiner, W.; Schlögl, K. Tetrahedron: Asymmetry 1993, 4, 285.
25. 2: C 73.03; H 6.33; N 2.84; Found: C 73.22; H 6.28; N 2.69.
26. The descriptor for the planar chirality is based on the CIP-rules. For a brief discussion on descriptors for planar chiral ferrocenes: Wagner, G.; Herrmann, R. In Ferrocenes; Togni, A.: Hayashi, T., Ed.; VCH Verlagsgesellschaft: Weinheim, 1995; p 173.
27. Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002. Sammakia, T.; Latham, H. A. J. Org. Chem. 1996, 61, 1629.
28. Sammakia, T.; Latham, H. A. J. Org. Chem. 1995, 60, 6002. Sammakia, T.; Latham, H. A. J. Org. Chem. 1996, 61, 1629.
29. Details of the crystal structure determination may be obtained from the Director of the Cambridge Crystallographic Data Center, Lensfield Road, Cambridge CB2 1EW (UK) on quoting the full journal citation.
30. Bolm, C.; Muñiz Fernández, K.; Seger, A.; Raabe, G. Manuscript in preparation.