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Volumn , Issue 16, 2008, Pages 2767-2773

Asymmetric epoxidation of trans-chalcones organocatalyzed by β-amino alcohols

Author keywords

Amino alcohols; Asymmetric synthesis; Epoxidation; Organocatalysis

Indexed keywords


EID: 53749108479     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800140     Document Type: Article
Times cited : (44)

References (64)
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    • Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
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    • Eds: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
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    • Jacobsen, E.N.1    Wu, M.H.2
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    • [13c]
    • [13c]
  • 41
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    • Primary amines, thanks to their reduced steric hindrance, form iminium ions more easily than secondary amines. For examples of asymmetric 1,4-addition reactions of nucleophiles to enones via iminium activation, see: a J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, R. Li, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. Int. Ed. 2007, 46, 389;
    • Primary amines, thanks to their reduced steric hindrance, form iminium ions more easily than secondary amines. For examples of asymmetric 1,4-addition reactions of nucleophiles to enones via iminium activation, see: a) J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, R. Li, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. Int. Ed. 2007, 46, 389;
  • 47
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    • In the reaction carried out in Table 3, Entry 12, the epoxidation was not completely depressed, as part of unprotonated catalyst 11e could promote the reaction
    • In the reaction carried out in Table 3, Entry 12, the epoxidation was not completely depressed, as part of unprotonated catalyst 11e could promote the reaction.
  • 48
    • 53749098896 scopus 로고    scopus 로고
    • Prolonged reaction time did not improve the conversion
    • Prolonged reaction time did not improve the conversion.
  • 50
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    • For a recent review on asymmetric epoxidation of electron-poor alkenes, see
    • For a recent review on asymmetric epoxidation of electron-poor alkenes, see: M. J. Porter, J. Skidmore, Chem. Commun. 2000, 1215.
    • (2000) Chem. Commun , pp. 1215
    • Porter, M.J.1    Skidmore, J.2
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    • If an iminium intermediate would have been formed between secondary amines 2c and 2d and trans-chalcone, a comparable level of asymmetric induction would have been expected for the epoxide, because the side chain would have offered the same steric hindrance for the peroxide approach.
    • If an iminium intermediate would have been formed between secondary amines 2c and 2d and trans-chalcone, a comparable level of asymmetric induction would have been expected for the epoxide, because the side chain would have offered the same steric hindrance for the peroxide approach.
  • 55
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    • See also Table 3, Entries 6 and 10.
    • See also Table 3, Entries 6 and 10.
  • 57
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    • Catalyst cis-9 (Table 3, Entry 4), whose ammonium ion has a dihedral θ angle close to 0° is indeed more active than trans-10 isomer, whose ammonium ion has a dihedral θ angle bigger than 100° (Table 3, Entry 5).
    • Catalyst cis-9 (Table 3, Entry 4), whose ammonium ion has a dihedral θ angle close to 0° is indeed more active than trans-10 isomer, whose ammonium ion has a dihedral θ angle bigger than 100° (Table 3, Entry 5).
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