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Volumn 41, Issue 14, 2000, Pages 2327-2331

The asymmetric hetero-Diels-Alder reaction of enamide aldehydes with Danishefsky's diene and an efficient synthesis of chiral binaphthyl ligands

Author keywords

Asymmetric; Binaphthyl; Catalysis; Hetero Diels Alder reactions

Indexed keywords

ALDEHYDE DERIVATIVE; NAPHTHYL GROUP;

EID: 0034175563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00193-3     Document Type: Article
Times cited : (29)

References (39)
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    • (b) Care is needed to avoid the polymerization of the enamide aldehydes
    • (b) Care is needed to avoid the polymerization of the enamide aldehydes.
  • 13
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    • 3) δ 9.62 (s, 1H), 7.29-7.54 (m, 10 H), 6.78 (d, J=10.2 Hz, 1H), 6.15 (d, J=10.2 Hz, 1H), 4.80 (d, J=17.4 Hz, 1H), 4.63 (d, J=17.4 Hz, 1H), 2.31-2.71 (m, 4H)
    • 3) δ 9.62 (s, 1H), 7.29-7.54 (m, 10 H), 6.78 (d, J=10.2 Hz, 1H), 6.15 (d, J=10.2 Hz, 1H), 4.80 (d, J=17.4 Hz, 1H), 4.63 (d, J=17.4 Hz, 1H), 2.31-2.71 (m, 4H).
  • 25
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    • 3) δ 7.60 (d, J=12.8 Hz, 1H), 7.30 (br s, 1H), 5.72 (br s, 1H), 5.57 (d, J=12.8 Hz, 1H), 4.62-4.68 (m, 2H), 3.71 (s, 3H), 2.58-2.85 (m, 2H), 2.08 (s, 3H), 0.13 (s, 9H)
    • 3) δ 7.60 (d, J=12.8 Hz, 1H), 7.30 (br s, 1H), 5.72 (br s, 1H), 5.57 (d, J=12.8 Hz, 1H), 4.62-4.68 (m, 2H), 3.71 (s, 3H), 2.58-2.85 (m, 2H), 2.08 (s, 3H), 0.13 (s, 9H).
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    • © For a recent review on the application of binaphthyl compounds, see
    • © For a recent review on the application of binaphthyl compounds, see: Pu, L. Chem. Rev. 1998, 98, 2405-2494.
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    • 9a, b.
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    • Selected examples on the asymmetric hydrogenation of enamides: (a)
    • Selected examples on the asymmetric hydrogenation of enamides: (a) Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117-7119. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084-6085. © Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem. 1998, 63, 8100-8101. (d) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808-5809.
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    • (b)
    • Selected examples on the asymmetric hydrogenation of enamides: (a) Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117-7119. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084-6085. © Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem. 1998, 63, 8100-8101. (d) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808-5809.
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    • ©
    • Selected examples on the asymmetric hydrogenation of enamides: (a) Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117-7119. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084-6085. © Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem. 1998, 63, 8100-8101. (d) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808-5809.
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    • (d)
    • Selected examples on the asymmetric hydrogenation of enamides: (a) Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117-7119. (b) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084-6085. © Zhu, G.; Casalnuovo, A. L.; Zhang, X. J. Org. Chem. 1998, 63, 8100-8101. (d) Zhang, F.-Y.; Pai, C.-C.; Chan, A. S. C. J. Am. Chem. Soc. 1998, 120, 5808-5809.
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    • Zhang, F.-Y.1    Pai, C.-C.2    Chan, A.S.C.3


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