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Volumn 8, Issue 4, 2006, Pages 637-640

Stereoselective synthesis of (E)-α,β-unsaturated esters via carbene-catalyzed redox esterification

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EID: 33644764723     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052826h     Document Type: Article
Times cited : (252)

References (53)
  • 1
    • 0041738169 scopus 로고    scopus 로고
    • Selected recent examples of application include 1,4-additions: (a) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829-2844.
    • (2003) Chem. Rev. , vol.103 , pp. 2829-2844
    • Hayashi, T.1    Yamasaki, K.2
  • 32
  • 42
    • 33644768766 scopus 로고    scopus 로고
    • note
    • An atom-efficient decarboxylative modification of the Doebner-Knoevenagel reaction for the generation of α,β-unsaturated esters using malonic acid half esters in the presence of catalytic amounts of base has been published recently by List and co-workers: refs 3c,d.
  • 46
    • 24944439544 scopus 로고    scopus 로고
    • It is noteworthy that homoenolate III seems not to undergo any C-C bond formation as a competing electrophilic trapping event as it is observed for alkenyl substrates that can yield homolactones depending on the reaction conditions. Sohn, S. S.; Bode, J. W. Org. Lett. 2005, 7, 3873-3876.
    • (2005) Org. Lett. , vol.7 , pp. 3873-3876
    • Sohn, S.S.1    Bode, J.W.2
  • 49
    • 0031037758 scopus 로고    scopus 로고
    • Only low selectivities (E/Z < 1:4) are observed in the final protonation event of 1,2,4-triazole-substituted ethoxy allenolate: Katritzky, A. R.; Feng, D.; Lang, H. J. Org. Chem. 1997, 62, 715-720.
    • (1997) J. Org. Chem. , vol.62 , pp. 715-720
    • Katritzky, A.R.1    Feng, D.2    Lang, H.3
  • 50
    • 33644762585 scopus 로고    scopus 로고
    • note
    • For details, see Supporting Information.
  • 51
    • 0038049457 scopus 로고    scopus 로고
    • IMes·HCl is commercially available (1 g ≈ $40). For its preparation, see: Arduengo, A. J., III. U.S. Patent 5,077,414, 1991. Triazolium precatalyst 5 was prepared according to a known procedure: Enders, D.; Breuer, K.; Kallfass, U.; Balensiefer, T. Synthesis 2003, 1292-1295.
    • (2003) Synthesis , pp. 1292-1295
    • Enders, D.1    Breuer, K.2    Kallfass, U.3    Balensiefer, T.4
  • 52
    • 33644746959 scopus 로고    scopus 로고
    • note
    • For an exemplary GC/MS of a crude reaction mixture (Table 1, entry 8), see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.