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Volumn 50, Issue 44, 2009, Pages 6040-6043

Iron chloride enhancement of dimethylzinc-mediated radical conjugate addition of ethers and an amine to alkylidenemalonates

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; AMINE; DIMETHYL SULFOXIDE; ETHER DERIVATIVE; FERROUS CHLORIDE; MALONIC ACID DERIVATIVE;

EID: 70149116122     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.034     Document Type: Article
Times cited : (13)

References (39)
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    • In: Gansäuer A. (Ed). Radicals in Synthesis I and II. Topics in Current Chemistry 263 and 264 (2006), Springer-Verlag, Berlin, Heidelberg
    • (2006) Topics in Current Chemistry 263 and 264
  • 2
    • 0004269715 scopus 로고    scopus 로고
    • Renaud P., and Sibi M.P. (Eds), Wiley-VCH, Weinheim
    • In: Renaud P., and Sibi M.P. (Eds). Radicals in Organic Synthesis Vols. 1 and 2 (2001), Wiley-VCH, Weinheim
    • (2001) Radicals in Organic Synthesis , vol.1-2
  • 15
    • 33846073628 scopus 로고    scopus 로고
    • Recent examples for conjugate addition of α-hydroxy or α-alkoxyalkyl radicals:
    • Recent examples for conjugate addition of α-hydroxy or α-alkoxyalkyl radicals:. Oka R., Nakayama M., Sakaguchi S., and Ishii Y. Chem. Lett. 35 (2006) 1104-1105
    • (2006) Chem. Lett. , vol.35 , pp. 1104-1105
    • Oka, R.1    Nakayama, M.2    Sakaguchi, S.3    Ishii, Y.4
  • 19
    • 55949093214 scopus 로고    scopus 로고
    • Our efforts to reduce a radical source by using iodoalkanes:
    • Our efforts to reduce a radical source by using iodoalkanes:. Yamada K., Nakano M., Maekawa M., Akindele T., and Tomioka K. Org. Lett. 10 (2008) 3805-3808
    • (2008) Org. Lett. , vol.10 , pp. 3805-3808
    • Yamada, K.1    Nakano, M.2    Maekawa, M.3    Akindele, T.4    Tomioka, K.5
  • 31
    • 54749149062 scopus 로고    scopus 로고
    • Iron catalyzed C-C bond formation between ether and diketone or β-ketoester:
    • Iron catalyzed C-C bond formation between ether and diketone or β-ketoester:. Li Z., Yu R., and Li H. Angew. Chem., Int. Ed. 47 (2008) 7497-7500
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 7497-7500
    • Li, Z.1    Yu, R.2    Li, H.3
  • 32
    • 51049122142 scopus 로고    scopus 로고
    • Copper-catalyzed conjugate addition is a well-known reaction. For examples, see: and references cited therein
    • Copper-catalyzed conjugate addition is a well-known reaction. For examples, see:. Alexakis A., Bäckvall J.E., Krause N., Pàmies O., and Diéguez M. Chem. Rev. 108 (2008) 2796-2823 and references cited therein
    • (2008) Chem. Rev. , vol.108 , pp. 2796-2823
    • Alexakis, A.1    Bäckvall, J.E.2    Krause, N.3    Pàmies, O.4    Diéguez, M.5
  • 34
    • 70149112230 scopus 로고    scopus 로고
    • note
    • 4,4,5,5-Tetramethyl-1,3-dioxolan-2-yl radical is more stable than THF-2-yl radical by ca. 1 kcal/mol in B3LYP/6-31G* level DFT calculations. This would be the reason for a more facile retro-reaction in the reaction of 4,4,5,5-tetramethyl-1,3-dioxolane.
  • 36
    • 70149100767 scopus 로고    scopus 로고
    • note
    • Although there is a possibility that alkoxyl radicals are generated from peroxides by the action of the iron salts, the suppressed production of 6 and 7 is not rationalized by the formation of alkoxyl radicals, which would only facilitate the generation of THF-2-yl radical and dioxolan-2-yl radical by hydrogen abstraction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.