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Volumn 56, Issue 18, 2000, Pages 2779-2788

Copper hydride-catalyzed tandem 1,4-reduction/alkylation reactions

Author keywords

Conjugate reduction; Copper hydride; Silyl hydrides

Indexed keywords

ALDEHYDE; COPPER DERIVATIVE; ETHER DERIVATIVE; FLUORIDE; HALIDE; SILANE DERIVATIVE;

EID: 0034724742     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00132-0     Document Type: Article
Times cited : (117)

References (25)
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    • For representative methods, see Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Meneses, R. Synlett 1999, 1663; Ikeno, T.; Kimura, T.; Ohtsuka, Y.; Yamada, T. Synlett 1999, 96; Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473; Boudjouk, P.; Choi, S.-B.; Hauck, B. J.; Rajkumar, A. B. Tetrahedron Lett. 1998, 39, 3951; Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585; Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1998, 38, 8887; Ravasio, N.; Antenori, M.; Gargano, M.; Mastrorilli, P. Tetrahedron Lett. 1996, 37, 3529; Evans, D.A.; Fu, G.C. J. Org. Chem. 1990, 55, 5678.
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    • For representative methods, see Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Meneses, R. Synlett 1999, 1663; Ikeno, T.; Kimura, T.; Ohtsuka, Y.; Yamada, T. Synlett 1999, 96; Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473; Boudjouk, P.; Choi, S.-B.; Hauck, B. J.; Rajkumar, A. B. Tetrahedron Lett. 1998, 39, 3951; Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585; Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1998, 38, 8887; Ravasio, N.; Antenori, M.; Gargano, M.; Mastrorilli, P. Tetrahedron Lett. 1996, 37, 3529; Evans, D.A.; Fu, G.C. J. Org. Chem. 1990, 55, 5678.
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    • Boudjouk, P.1    Choi, S.-B.2    Hauck, B.J.3    Rajkumar, A.B.4
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    • For representative methods, see Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Meneses, R. Synlett 1999, 1663; Ikeno, T.; Kimura, T.; Ohtsuka, Y.; Yamada, T. Synlett 1999, 96; Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473; Boudjouk, P.; Choi, S.-B.; Hauck, B. J.; Rajkumar, A. B. Tetrahedron Lett. 1998, 39, 3951; Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585; Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1998, 38, 8887; Ravasio, N.; Antenori, M.; Gargano, M.; Mastrorilli, P. Tetrahedron Lett. 1996, 37, 3529; Evans, D.A.; Fu, G.C. J. Org. Chem. 1990, 55, 5678.
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    • Ito, H.1    Ishizuka, T.2    Arimoto, K.3    Miura, K.4    Hosomi, A.5
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    • For representative methods, see Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Meneses, R. Synlett 1999, 1663; Ikeno, T.; Kimura, T.; Ohtsuka, Y.; Yamada, T. Synlett 1999, 96; Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473; Boudjouk, P.; Choi, S.-B.; Hauck, B. J.; Rajkumar, A. B. Tetrahedron Lett. 1998, 39, 3951; Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585; Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1998, 38, 8887; Ravasio, N.; Antenori, M.; Gargano, M.; Mastrorilli, P. Tetrahedron Lett. 1996, 37, 3529; Evans, D.A.; Fu, G.C. J. Org. Chem. 1990, 55, 5678.
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    • Ravasio, N.1    Antenori, M.2    Gargano, M.3    Mastrorilli, P.4
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    • For representative methods, see Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Meneses, R. Synlett 1999, 1663; Ikeno, T.; Kimura, T.; Ohtsuka, Y.; Yamada, T. Synlett 1999, 96; Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473; Boudjouk, P.; Choi, S.-B.; Hauck, B. J.; Rajkumar, A. B. Tetrahedron Lett. 1998, 39, 3951; Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585; Ito, H.; Ishizuka, T.; Arimoto, K.; Miura, K.; Hosomi, A. Tetrahedron Lett. 1998, 38, 8887; Ravasio, N.; Antenori, M.; Gargano, M.; Mastrorilli, P. Tetrahedron Lett. 1996, 37, 3529; Evans, D.A.; Fu, G.C. J. Org. Chem. 1990, 55, 5678.
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    • Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291; See also Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677; Stryker, J. M., Mahoney, W. S., Daeuble, J. F., Brestensky, D. M. In Catalysis in Organic Synthesis; Pascoe, W. E., Ed.; Marcel Dekker: New York, 1992; pp 29-44.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 5677
    • Brestensky, D.M.1    Stryker, J.M.2
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    • Pascoe, W. E., Ed.; Marcel Dekker: New York
    • Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291; See also Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1989, 30, 5677; Stryker, J. M., Mahoney, W. S., Daeuble, J. F., Brestensky, D. M. In Catalysis in Organic Synthesis; Pascoe, W. E., Ed.; Marcel Dekker: New York, 1992; pp 29-44.
    • (1992) In Catalysis in Organic Synthesis; , pp. 29-44
    • Stryker, J.M.1    Mahoney, W.S.2    Daeuble, J.F.3    Brestensky, D.M.4
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    • This sample still contains unknown impurities, one of which may be triphenylphosphine oxide, possibly the major contaminant in the Aldrich samples. This material can be removed by an additional recrystallization, although this was unnecessary for our purposes; Personal communication
    • This sample still contains unknown impurities, one of which may be triphenylphosphine oxide, possibly the major contaminant in the Aldrich samples. This material can be removed by an additional recrystallization, although this was unnecessary for our purposes; Stryker, J. M. Personal communication.
    • Stryker, J.M.1
  • 24
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    • Curiously, all attempts at conjugate reduction of an α,β-unsaturated ester or lactone (e.g. methyl cinnamate and coumarin) were fruitless, as no reaction was observed irrespective of catalyst amount or silyl hydride.
    • Curiously, all attempts at conjugate reduction of an α,β-unsaturated ester or lactone (e.g. methyl cinnamate and coumarin) were fruitless, as no reaction was observed irrespective of catalyst amount or silyl hydride.


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