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Volumn 56, Issue 18, 2000, Pages 2857-2863

Approach to enantioselective conjugate addition of organocopper reagents to cycloalkenones by the aid of chiral lactam bearing phosphine group

Author keywords

Asymmetric reactions; Catalysis; Conjugate additions; Organometals

Indexed keywords

COPPER DERIVATIVE; CYCLOALKANE DERIVATIVE; DIETHYLZINC; LACTAM DERIVATIVE; MAGNESIUM DERIVATIVE; ORGANOMETALLIC COMPOUND; PHOSPHINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

EID: 0034725032     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00141-1     Document Type: Article
Times cited : (37)

References (46)
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  • 26
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    • For the use of dialkylzinc in the conjugate addition, see: (a)
    • For the use of dialkylzinc in the conjugate addition, see: (a) Soai, K.; Hayasaka, T.; Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516. (b) Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427. (c) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305. (d) de Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1467-1470.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 516
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  • 27
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    • (b)
    • For the use of dialkylzinc in the conjugate addition, see: (a) Soai, K.; Hayasaka, T.; Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516. (b) Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427. (c) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305. (d) de Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1467-1470.
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  • 28
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    • (c)
    • For the use of dialkylzinc in the conjugate addition, see: (a) Soai, K.; Hayasaka, T.; Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516. (b) Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427. (c) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305. (d) de Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1467-1470.
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  • 29
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    • (d)
    • For the use of dialkylzinc in the conjugate addition, see: (a) Soai, K.; Hayasaka, T.; Ugajin, S. J. Chem. Soc., Chem. Commun. 1989, 516. (b) Alexakis, A.; Frutos, J.; Mangeney, P. Tetrahedron: Asymmetry 1993, 4, 2427. (c) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305. (d) de Vries, A. H. M.; Imbos, R.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 1467-1470.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1467-1470
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  • 32
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    • The ee and absolute configuration were determined as had been reported previously (Refs. 17-19).
    • The ee and absolute configuration were determined as had been reported previously (Refs. 17-19).
  • 35
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    • (a) See, Ref. 8.
    • (a) See, Ref. 8.
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    • 15: Corey, E. J.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. 16: Nakai, T.; Fujimoto, K. Heterocycles 1996, 42, 423-436. 17: Hosino, O.; Murakata, M. Tetrahedron: Asymmetry 1998, 9, 2087-2092.
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    • 16:
    • 15: Corey, E. J.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. 16: Nakai, T.; Fujimoto, K. Heterocycles 1996, 42, 423-436. 17: Hosino, O.; Murakata, M. Tetrahedron: Asymmetry 1998, 9, 2087-2092.
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    • 15: Corey, E. J.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495. 16: Nakai, T.; Fujimoto, K. Heterocycles 1996, 42, 423-436. 17: Hosino, O.; Murakata, M. Tetrahedron: Asymmetry 1998, 9, 2087-2092.
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    • 3 unless otherwise noted. Chemical shift (δ) was presented in ppm relative to internal tetramethylsilane. Coupling constant value (J) was presented in Hz. Mass spectra were measured by EI mode unless otherwise noted.
    • 3 unless otherwise noted. Chemical shift (δ) was presented in ppm relative to internal tetramethylsilane. Coupling constant value (J) was presented in Hz. Mass spectra were measured by EI mode unless otherwise noted.


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