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Volumn 7, Issue 13, 2005, Pages 2579-2582

Enantioselective epoxidation of α,β-enones promoted by α,α-diphenyl-L-prolinol as bifunctional organocatalyst

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL; BIPHENYL DERIVATIVE; EPOXIDE; KETONE; PROLINOL; PYRROLIDINE DERIVATIVE;

EID: 28544451072     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050694m     Document Type: Article
Times cited : (127)

References (52)
  • 23
    • 0034750244 scopus 로고    scopus 로고
    • For reviews on organocatalysis, see: (a) List, B. Synlett 2001, 1675.
    • (2001) Synlett , pp. 1675
    • List, B.1
  • 26
    • 4143094833 scopus 로고    scopus 로고
    • Asymmetric Organocatalysis
    • (d) Special Issue: Asymmetric Organocatalysis, Acc. Chem. Res. 2004, 37, 487.
    • (2004) Acc. Chem. Res. , vol.37 , Issue.SPEC. ISSUE , pp. 487
  • 34
    • 29844447225 scopus 로고    scopus 로고
    • Jpn. Patent JP 06092950 A2, 1994
    • Amino alcohols have been previously reported to promote, in stoichiometric amounts, the epoxidation of electron-deficient alkenes to racemic epoxides: Masahiko, Y.; Noboru, K.; Satomi, T. Jpn. Patent JP 06092950 A2, 1994.
    • Masahiko, Y.1    Noboru, K.2    Satomi, T.3
  • 35
    • 29844434166 scopus 로고    scopus 로고
    • note
    • The s-trans conformation of the enone moiety might be preferentially adopted in the epoxidation reaction, although a noncoplanar enone geometry cannot be excluded.
  • 39
    • 29844454394 scopus 로고    scopus 로고
    • note
    • Activation of the enone via iminium ion formation is less reasonably expected to occur under these reaction conditions, given the unreactive nature of enone carbonyls and the absence of an acid catalyst.
  • 42
    • 0000163641 scopus 로고
    • Wynberg first reported a transition-state complex comprising all three species (thiol, enone, and the catalyst) in the asymmetric Michael addition of thiols to cyclic enones mediated by quinine as bifunctional catalyst: Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 417
    • Hiemstra, H.1    Wynberg, H.2
  • 43
    • 4544221552 scopus 로고    scopus 로고
    • For studies on hydrogen bonds acting in a Lewis acid fashion, see: (a) Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 2062
    • Pihko, P.M.1
  • 51
    • 29844452499 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the crude reaction mixture showed no significant degradation of 2 under the reaction conditions.
  • 52
    • 29844448720 scopus 로고    scopus 로고
    • note
    • The epoxidation of 4a with the tertiary N-benzyl L-prolinol under the usual conditions (rt, hexane, TBHP, 90 h) furnished traces of the epoxide.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.