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Volumn 13, Issue 10, 2011, Pages 2586-2589

Phosphine-catalyzed β′-umpolung addition of nucleophiles to activated α-alkyl allenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; PHOSPHINE; PHOSPHINE DERIVATIVE;

EID: 79956155927     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200697m     Document Type: Article
Times cited : (59)

References (61)
  • 15
    • 0001334123 scopus 로고    scopus 로고
    • Albeit not in catalytic form, Cristau first demonstrated the γ-umpolung addition of nucleophiles to activated allenes; see:; Tetrahedron Lett. 1982, 23, 1569
    • Trost, B. M.; Drake, G. R. J. Org. Chem. 1997, 62, 5670 Albeit not in catalytic form, Cristau first demonstrated the γ-umpolung addition of nucleophiles to activated allenes; see: Cristau, H.-J.; Viala, J.; Christol, H. Tetrahedron Lett. 1982, 23, 1569
    • (1997) J. Org. Chem. , vol.62 , pp. 5670
    • Trost, B.M.1    Drake, G.R.2    Cristau, H.-J.3    Viala, J.4    Christol, H.5
  • 40
    • 0003094082 scopus 로고
    • 1H NMR spectra of the crude products. The characteristics of the isolated adduct matched those reported in the literature; see
    • 1H NMR spectra of the crude products. The characteristics of the isolated adduct matched those reported in the literature; see: Mandai, T.; Yokoyama, H.; Miki, T.; Fukuda, H.; Kobata, H.; Kawada, M.; Otera, J. Chem. Lett. 1980, 1057
    • (1980) Chem. Lett. , pp. 1057
    • Mandai, T.1    Yokoyama, H.2    Miki, T.3    Fukuda, H.4    Kobata, H.5    Kawada, M.6    Otera, J.7
  • 41
    • 0016197944 scopus 로고
    • Compound 1r contains the phenoxy phenyl propylamine skeleton found in a number of pharmaceuticals (e.g., the antidepressant fluoxetine); see
    • Compound 1r contains the phenoxy phenyl propylamine skeleton found in a number of pharmaceuticals (e.g., the antidepressant fluoxetine); see: Wong, D. T.; Horng, J. S.; Bymaster, F. P.; Hauser, K. L.; Molloy, B. B. Life Sciences 1974, 15, 471
    • (1974) Life Sciences , vol.15 , pp. 471
    • Wong, D.T.1    Horng, J.S.2    Bymaster, F.P.3    Hauser, K.L.4    Molloy, B.B.5
  • 47
    • 0007279543 scopus 로고
    • (E)-Ethyl 2-acetoxy-2-butenoate (3a) is an intermediate for the synthesis of mikanecic acid; see
    • (E)-Ethyl 2-acetoxy-2-butenoate (3a) is an intermediate for the synthesis of mikanecic acid; see: Edwards, J. D.; Matsumoto, T.; Hase, T. J. Org. Chem. 1967, 32, 244
    • (1967) J. Org. Chem. , vol.32 , pp. 244
    • Edwards, J.D.1    Matsumoto, T.2    Hase, T.3
  • 48
    • 79956123976 scopus 로고    scopus 로고
    • No epimerization occurred during the reaction, as verified through HPLC analysis; see the Supporting Information for details.
    • No epimerization occurred during the reaction, as verified through HPLC analysis; see the Supporting Information for details.
  • 49
    • 79956119991 scopus 로고    scopus 로고
    • Lu has reported that tributylphosphine facilitates γ-umpolung addition of dimethyl malonate to ethyl α-methyl allenoate; see ref 3a.
    • Lu has reported that tributylphosphine facilitates γ-umpolung addition of dimethyl malonate to ethyl α-methyl allenoate; see ref 3a.
  • 50
    • 79956108603 scopus 로고    scopus 로고
    • Lu has reported that benzyl alcohol functions as a γ-umpolung donor when reacted with allenoates; see ref 3a.
    • Lu has reported that benzyl alcohol functions as a γ-umpolung donor when reacted with allenoates; see ref 3a.
  • 55
    • 20344382286 scopus 로고    scopus 로고
    • For the synthesis of 3,4-dimethylcoumarin, see
    • For the synthesis of 3,4-dimethylcoumarin, see: Dittmer, D. C.; Li, Q.; Avilov, D. V. J. Org. Chem. 2005, 70, 4682
    • (2005) J. Org. Chem. , vol.70 , pp. 4682
    • Dittmer, D.C.1    Li, Q.2    Avilov, D.V.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.