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Volumn 348, Issue 3, 2006, Pages 339-346

Bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol: An improved organocatalyst for the asymmetric epoxidation of α,β-enones

Author keywords

, enones; Amino alcohols; Asymmetric epoxidation; Epoxides; Organic catalysis

Indexed keywords


EID: 33644606047     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505370     Document Type: Article
Times cited : (77)

References (60)
  • 21
    • 0003445429 scopus 로고    scopus 로고
    • (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin
    • b) Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999;
    • (1999) Comprehensive Asymmetric Catalysis
  • 28
    • 0030523674 scopus 로고    scopus 로고
    • For examples on the influence of electronic and inductive effects on reactivity, see: a) K. Bowden, E. J. Grubbs, Chem. Soc. Rev. 1996,171;
    • (1996) Chem. Soc. Rev. , pp. 171
    • Bowden, K.1    Grubbs, E.J.2
  • 35
    • 33644602729 scopus 로고    scopus 로고
    • note
    • [8] Polar, protic and coordinating solvents were detrimental for the reactivity and the enantioselectivity, which is consistent with a strong effect on ion-pairing as well as on hydrogen bonding interaction.
  • 36
    • 0346865819 scopus 로고    scopus 로고
    • For reviews on hydrogen bonding acting in weak Lewis acid fashion, see: a) P. R. Schreiner, Chem. Soc. Rev. 2003. 32, 289;
    • (2003) Chem. Soc. Rev. , vol.32 , pp. 289
    • Schreiner, P.R.1
  • 41
    • 0030964434 scopus 로고    scopus 로고
    • Most of the protocols for the asymmetric epoxidation of á,â-enones are highly enantioselective exclusively for chalcones as substrates, with the exception of the following procedures: a) M. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329;
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2329
    • Bougauchi, M.1    Watanabe, S.2    Arai, T.3    Sasai, H.4    Shibasaki, M.5
  • 43
    • 33644598287 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis (400 MHz) of the crude reaction mixture.
  • 44
    • 33644603196 scopus 로고    scopus 로고
    • note
    • 6, as a result of the activation by hydrogen bonding with 3g, since the interaction might be very weak.
  • 45
    • 33644586847 scopus 로고    scopus 로고
    • note
    • [8]
  • 46
    • 33644584865 scopus 로고    scopus 로고
    • note
    • The negative charge of the enolate, developed in the transition state at the oxygen of the carbonyl group after the nucleophilic attack at the β-carbon, would be poorly stabilized in apolar hexane, and consequently the formation of the enolate disfavoured. However, in this case, it can be efficiently stabilized by hydrogen bonding and electrostatic interaction with the positively charged nitrogen of the catalyst.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.