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Volumn 72, Issue 24, 2007, Pages 9372-9375

The O-acylation of ketone enolates by allyl 1H-imidazole-1-carboxylate mediated with boron trifluoride etherate - A convenient procedure for the synthesis of substituted allyl enol carbonates

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ENOL CARBONATES; BORON TRIFLUORIDE ETHERATE;

EID: 36649010386     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7016313     Document Type: Article
Times cited : (18)

References (32)
  • 1
    • 36649008445 scopus 로고    scopus 로고
    • For reviews concerning Pd-catalyzed decarboxylative asymmetric allylic alkylation of ketone enol carbonates and β-keto esters, see: (a) You, S.-L, Dai, L.-X. Angew. Chem, Int. Ed. 2006, 45, 5346
    • For reviews concerning Pd-catalyzed decarboxylative asymmetric allylic alkylation of ketone enol carbonates and β-keto esters, see: (a) You, S.-L.; Dai, L.-X. Angew. Chem., Int. Ed. 2006, 45, 5346.
  • 3
    • 33645450395 scopus 로고    scopus 로고
    • 661. For recent publications, see
    • (c) Braun, M.; Meier, T. Synlett 2006, 5, 661. For recent publications, see:
    • (2006) Synlett , vol.5
    • Braun, M.1    Meier, T.2
  • 15
    • 0000931564 scopus 로고    scopus 로고
    • In the reaction of Pd-catalyzed decarboxylative allylic alkylation of ketones to generate tertiary centers, the reaction mechanisms of allyl enol carbonates and that of allyl β-keto esters may be different: Intermediate I from enol carbonates can only undergo decarboxylation to afford Pd enolate II which recombines to the product. Intermediate III from β-keto esters, however, may undergo a facile H-shift to generate IV depending on the acidity of the α-proton. IV recombines to a β-keto acid V, which decarboxylates to the product. Therefore, allyl β-keto esters cannot completely replace enol allyl carbonates in this reaction. See: (a) Tsuji, J, Minami, I. Acc. Chem. Res. 1987, 20, 140
    • In the reaction of Pd-catalyzed decarboxylative allylic alkylation of ketones to generate tertiary centers, the reaction mechanisms of allyl enol carbonates and that of allyl β-keto esters may be different: Intermediate I from enol carbonates can only undergo decarboxylation to afford Pd enolate II which recombines to the product. Intermediate III from β-keto esters, however, may undergo a facile H-shift to generate IV depending on the acidity of the α-proton. IV recombines to a β-keto acid V, which decarboxylates to the product. Therefore, allyl β-keto esters cannot completely replace enol allyl carbonates in this reaction. See: (a) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
  • 22
    • 36649022124 scopus 로고
    • For review concerning the application of imidazolides as acylating agents, see
    • (a) For review concerning the application of imidazolides as acylating agents, see: Staab, H. A. Angew. Chem., Int. Ed. Engl. 1962, 7, 350.
    • (1962) Angew. Chem., Int. Ed. Engl , vol.7 , pp. 350
    • Staab, H.A.1
  • 30
    • 0041572010 scopus 로고    scopus 로고
    • For reference concerning the much better reactivity of acylimidazolium salts than the corresponding imidazolides, see: (a) Anders, E, Will, W. Tetrahedron Lett. 1978, 41, 3911
    • For reference concerning the much better reactivity of acylimidazolium salts than the corresponding imidazolides, see: (a) Anders, E.; Will, W. Tetrahedron Lett. 1978, 41, 3911.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.