An Efficient Asymmetric Synthesis of 2-Substituted Ferrocenecarboxaldehydes

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6733-6745

  Riant, Olivier ^a   Samuel, Odile ^a   Flessner, Timo ^a   Taudien, Stephan ^a   Kagan, Henri B ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000715061     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970075u     Document Type: Article

References (81)

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22. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
23. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
24. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
25. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
26. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
27. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
28. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
29. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
30. A similar strategy has been applied by others in the cymanthrene and benchrothrene series, see (a) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1991, 56, 7199. (b) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Dokl. Akad. Nauk. SSSR 1991, 320, 1123. (c) Aubé, J.; Heppert, J. A.; Milligan, M. L.; Smith, M. J., Zenk, P. J. Org. Chem. 1992, 57, 3563. (d) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I.; Turdybekov,K. M.; Struchnov, Y. T. J. Organometal. Chem. USSR (Engl.) 1992, 5, 575. (e) Kondo, Y.; Green, J. R.; Ho, J. J. Org. Chem. 1993, 58, 6182. (f) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. Russ. Chem. Bull. 1993, 42, 166. (g) Loim, N. M.; Kondratenko, M. A.; Sokolov, V. I. J. Org. Chem. 1994, 59, 7485. (h) Alexakis, A.; Kanger, T.; Mangeney, P.; Rose-Munch, F.; Perrotey, A.; Rose, E. Tetrahedron: Asymmetry 1995, 6, 47. (i) Uemura, M.; Daimon, A.; Hayashi, Y. J. Chem. Soc., Chem. Commun. 1995, 1943.
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58. Some chiral amino ferrocenes have been obtained starting from the corresponding carboxylic acid through a Curtius rearrangement, see for instance (a) Lehner, H.; Schlögl, K. Monat. Chem. 1970, 101, 895. (b) Rapic, V.; Schlögl, K.; Steinitz, B. Monat. Chem. 1977, 108, 767. Aminoferrocene has been prepared by reaction of copper phthalimide on ferroceneboronic acid followed by deprotection of the phthalide derivative, see: Montserrat, N.; Parkins, A. W.; Tomkins, A. R. J. Chem. Res. (S) 1995, 336. For a preparation involving the reaction of the sodium salt of an amide on bromoferrocene in the presence of a copper(I) salt, see: Herberhold, M.; Ellinger, M.; Kremnitz J. Organomet. Chem. 1983, 24, 227.
59. Some chiral amino ferrocenes have been obtained starting from the corresponding carboxylic acid through a Curtius rearrangement, see for instance (a) Lehner, H.; Schlögl, K. Monat. Chem. 1970, 101, 895. (b) Rapic, V.; Schlögl, K.; Steinitz, B. Monat. Chem. 1977, 108, 767. Aminoferrocene has been prepared by reaction of copper phthalimide on ferroceneboronic acid followed by deprotection of the phthalide derivative, see: Montserrat, N.; Parkins, A. W.; Tomkins, A. R. J. Chem. Res. (S) 1995, 336. For a preparation involving the reaction of the sodium salt of an amide on bromoferrocene in the presence of a copper(I) salt, see: Herberhold, M.; Ellinger, M.; Kremnitz J. Organomet. Chem. 1983, 24, 227.
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