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Volumn 68, Issue 11, 2003, Pages 4151-4157

Direct enantioselective Michael addition of aldehydes to vinyl ketones catalyzed by chiral amines

Author keywords

[No Author keywords available]

Indexed keywords

VINYL KETONES;

EID: 0038779504     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026837p     Document Type: Article
Times cited : (169)

References (67)
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    • For recent reviews on asymmetric organocatalysis, see: (a) List, B. Tetrahedron 2002, 58, 5573. (b) Gröger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529. (c) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (d) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 529
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    • For recent reviews on asymmetric organocatalysis, see: (a) List, B. Tetrahedron 2002, 58, 5573. (b) Gröger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529. (c) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (d) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
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    • For recent reviews on asymmetric organocatalysis, see: (a) List, B. Tetrahedron 2002, 58, 5573. (b) Gröger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529. (c) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726. (d) Jarvo, E. R.; Miller, S. J. Tetrahedron 2002, 58, 2481.
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    • For nonenantioselective direct catalytic 1,4-conjugated addition of aldehydes to vinyl ketones, see: (a) Hagiwara, H.; Komatsubara, N.; Ono, H.; Okabe, T.; Hoshi, T.; Suzuki, T.; Ando, M.; Kato, M. J. Chem. Soc., Perkin Trans. 1 2001, 316. (b) Hagiwara, H.; Okabe, T.; Hakoda, T.; Hoshi, T.; Ono, H.; Kamat, V. P.; Suzuki, T.; Ando, M. Tetrahedron Lett. 2001, 42, 2705. (c) Shimizu, K.; Suzuki, H.; Hayashi, E.; Kodama, T.; Tsuchiya, Y.; Hagiwara, H.; Kitayama, Y. Chem. Commun. 2002, 1068. See also Yamada and Otani (d) Yamada, S.-i.; Otani, G. Tetrahedron Lett. 1969, 48, 4237] for stoichiometric reactions of chiral enamines with methyl vinyl ketone; in this study up to 50% ee optical yield was obtained. For related catalytic enantioselective approaches see also: (e) Kim, S.-G.; Ahn, K. H. Tetrahedron Lett. 2001, 42, 4175. (f) Evans, D. A.; Scheidt, K. A.; Johnson, J. N. J. Am. Chem. Soc. 2001, 123, 4480.
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    • For nonenantioselective direct catalytic 1,4-conjugated addition of aldehydes to vinyl ketones, see: (a) Hagiwara, H.; Komatsubara, N.; Ono, H.; Okabe, T.; Hoshi, T.; Suzuki, T.; Ando, M.; Kato, M. J. Chem. Soc., Perkin Trans. 1 2001, 316. (b) Hagiwara, H.; Okabe, T.; Hakoda, T.; Hoshi, T.; Ono, H.; Kamat, V. P.; Suzuki, T.; Ando, M. Tetrahedron Lett. 2001, 42, 2705. (c) Shimizu, K.; Suzuki, H.; Hayashi, E.; Kodama, T.; Tsuchiya, Y.; Hagiwara, H.; Kitayama, Y. Chem. Commun. 2002, 1068. See also Yamada and Otani (d) Yamada, S.-i.; Otani, G. Tetrahedron Lett. 1969, 48, 4237] for stoichiometric reactions of chiral enamines with methyl vinyl ketone; in this study up to 50% ee optical yield was obtained. For related catalytic enantioselective approaches see also: (e) Kim, S.-G.; Ahn, K. H. Tetrahedron Lett. 2001, 42, 4175. (f) Evans, D. A.; Scheidt, K. A.; Johnson, J. N. J. Am. Chem. Soc. 2001, 123, 4480.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2705
    • Hagiwara, H.1    Okabe, T.2    Hakoda, T.3    Hoshi, T.4    Ono, H.5    Kamat, V.P.6    Suzuki, T.7    Ando, M.8
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    • See also Yamada and Otani
    • For nonenantioselective direct catalytic 1,4-conjugated addition of aldehydes to vinyl ketones, see: (a) Hagiwara, H.; Komatsubara, N.; Ono, H.; Okabe, T.; Hoshi, T.; Suzuki, T.; Ando, M.; Kato, M. J. Chem. Soc., Perkin Trans. 1 2001, 316. (b) Hagiwara, H.; Okabe, T.; Hakoda, T.; Hoshi, T.; Ono, H.; Kamat, V. P.; Suzuki, T.; Ando, M. Tetrahedron Lett. 2001, 42, 2705. (c) Shimizu, K.; Suzuki, H.; Hayashi, E.; Kodama, T.; Tsuchiya, Y.; Hagiwara, H.; Kitayama, Y. Chem. Commun. 2002, 1068. See also Yamada and Otani (d) Yamada, S.-i.; Otani, G. Tetrahedron Lett. 1969, 48, 4237] for stoichiometric reactions of chiral enamines with methyl vinyl ketone; in this study up to 50% ee optical yield was obtained. For related catalytic enantioselective approaches see also: (e) Kim, S.-G.; Ahn, K. H. Tetrahedron Lett. 2001, 42, 4175. (f) Evans, D. A.; Scheidt, K. A.; Johnson, J. N. J. Am. Chem. Soc. 2001, 123, 4480.
    • (2002) Chem. Commun. , pp. 1068
    • Shimizu, K.1    Suzuki, H.2    Hayashi, E.3    Kodama, T.4    Tsuchiya, Y.5    Hagiwara, H.6    Kitayama, Y.7
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    • For nonenantioselective direct catalytic 1,4-conjugated addition of aldehydes to vinyl ketones, see: (a) Hagiwara, H.; Komatsubara, N.; Ono, H.; Okabe, T.; Hoshi, T.; Suzuki, T.; Ando, M.; Kato, M. J. Chem. Soc., Perkin Trans. 1 2001, 316. (b) Hagiwara, H.; Okabe, T.; Hakoda, T.; Hoshi, T.; Ono, H.; Kamat, V. P.; Suzuki, T.; Ando, M. Tetrahedron Lett. 2001, 42, 2705. (c) Shimizu, K.; Suzuki, H.; Hayashi, E.; Kodama, T.; Tsuchiya, Y.; Hagiwara, H.; Kitayama, Y. Chem. Commun. 2002, 1068. See also Yamada and Otani (d) Yamada, S.-i.; Otani, G. Tetrahedron Lett. 1969, 48, 4237] for stoichiometric reactions of chiral enamines with methyl vinyl ketone; in this study up to 50% ee optical yield was obtained. For related catalytic enantioselective approaches see also: (e) Kim, S.-G.; Ahn, K. H. Tetrahedron Lett. 2001, 42, 4175. (f) Evans, D. A.; Scheidt, K. A.; Johnson, J. N. J. Am. Chem. Soc. 2001, 123, 4480.
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    • For nonenantioselective direct catalytic 1,4-conjugated addition of aldehydes to vinyl ketones, see: (a) Hagiwara, H.; Komatsubara, N.; Ono, H.; Okabe, T.; Hoshi, T.; Suzuki, T.; Ando, M.; Kato, M. J. Chem. Soc., Perkin Trans. 1 2001, 316. (b) Hagiwara, H.; Okabe, T.; Hakoda, T.; Hoshi, T.; Ono, H.; Kamat, V. P.; Suzuki, T.; Ando, M. Tetrahedron Lett. 2001, 42, 2705. (c) Shimizu, K.; Suzuki, H.; Hayashi, E.; Kodama, T.; Tsuchiya, Y.; Hagiwara, H.; Kitayama, Y. Chem. Commun. 2002, 1068. See also Yamada and Otani (d) Yamada, S.-i.; Otani, G. Tetrahedron Lett. 1969, 48, 4237] for stoichiometric reactions of chiral enamines with methyl vinyl ketone; in this study up to 50% ee optical yield was obtained. For related catalytic enantioselective approaches see also: (e) Kim, S.-G.; Ahn, K. H. Tetrahedron Lett. 2001, 42, 4175. (f) Evans, D. A.; Scheidt, K. A.; Johnson, J. N. J. Am. Chem. Soc. 2001, 123, 4480.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4175
    • Kim, S.-G.1    Ahn, K.H.2
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    • 0034817259 scopus 로고    scopus 로고
    • For nonenantioselective direct catalytic 1,4-conjugated addition of aldehydes to vinyl ketones, see: (a) Hagiwara, H.; Komatsubara, N.; Ono, H.; Okabe, T.; Hoshi, T.; Suzuki, T.; Ando, M.; Kato, M. J. Chem. Soc., Perkin Trans. 1 2001, 316. (b) Hagiwara, H.; Okabe, T.; Hakoda, T.; Hoshi, T.; Ono, H.; Kamat, V. P.; Suzuki, T.; Ando, M. Tetrahedron Lett. 2001, 42, 2705. (c) Shimizu, K.; Suzuki, H.; Hayashi, E.; Kodama, T.; Tsuchiya, Y.; Hagiwara, H.; Kitayama, Y. Chem. Commun. 2002, 1068. See also Yamada and Otani (d) Yamada, S.-i.; Otani, G. Tetrahedron Lett. 1969, 48, 4237] for stoichiometric reactions of chiral enamines with methyl vinyl ketone; in this study up to 50% ee optical yield was obtained. For related catalytic enantioselective approaches see also: (e) Kim, S.-G.; Ahn, K. H. Tetrahedron Lett. 2001, 42, 4175. (f) Evans, D. A.; Scheidt, K. A.; Johnson, J. N. J. Am. Chem. Soc. 2001, 123, 4480.
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    • note
    • It should be noted that the priority of the 5-keto aldehydes changes for the different aldehydes.
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    • For a review about nonlinear effects see e.g.: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922. It should also be noted that the first paper by Kagan et al. dealing with nonlinear effects was about proline-catalyzed intramolecular aldol reactions: (b) Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353.
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    • For a review about nonlinear effects see e.g.: (a) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2922. It should also be noted that the first paper by Kagan et al. dealing with nonlinear effects was about proline-catalyzed intramolecular aldol reactions: (b) Puchot, C.; Samuel, O.; Duñach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 2353
    • Puchot, C.1    Samuel, O.2    Duñach, E.3    Zhao, S.4    Agami, C.5    Kagan, H.B.6
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    • note
    • The reactions were carried out under neat conditions.


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