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Volumn 18, Issue 30, 2012, Pages 9221-9224

Copper(I)-catalyzed [3+1] cycloaddition of alkenyldiazoacetates and iminoiodinanes: Easy access to substituted 2-azetines

Author keywords

2 azetines; carbenes; copper catalysts; cycloaddition; diazo compounds; iminoiodinanes

Indexed keywords

2-AZETINES; CARBENES; COPPER CATALYST; DIAZO COMPOUNDS; IMINOIODINANES;

EID: 84863886391     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200998     Document Type: Article
Times cited : (38)

References (33)
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    • For a recent Review on the synthesis of azetidinones and azetidines, see
    • For a recent Review on the synthesis of azetidinones and azetidines, see:, A. Brandi, S. Cicchi, F. M. Cordero, Chem. Rev. 2008, 108, 3988.
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    • 2-Azetine derivatives are known to undergo spontaneous electrocyclic ring opening to afford the 1-azadiene isomers. For a recent example, see
    • 2-Azetine derivatives are known to undergo spontaneous electrocyclic ring opening to afford the 1-azadiene isomers. For a recent example, see:, N. Shindoh, K. Kitaura, Y. Takemoto, K. Takasu, J. Am. Chem. Soc. 2011, 133, 8470.
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    • For specific syntheses of stable 2-azetine derivatives, see
    • For specific syntheses of stable 2-azetine derivatives, see
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    • For seminal contributions to the field of copper-catalyzed aziridination of alkenes, see
    • For seminal contributions to the field of copper-catalyzed aziridination of alkenes, see
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    • For select studies on the applications of vinyldiazoacetates in the synthesis of five- to seven-membered nitrogen heterocycles, see
    • For select studies on the applications of vinyldiazoacetates in the synthesis of five- to seven-membered nitrogen heterocycles, see
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    • We recently reported that a copper(II)-catalyzed reaction of vinyl diazo derivatives and iodosylbenzene (O=I-Ph) does not lead to oxygen heterocycles, but rather β-oxodiazo compounds resulting from a novel oxidative rearrangement were formed
    • We recently reported that a copper(II)-catalyzed reaction of vinyl diazo derivatives and iodosylbenzene (O=I-Ph) does not lead to oxygen heterocycles, but rather β-oxodiazo compounds resulting from a novel oxidative rearrangement were formed:, J. Barluenga, G. Lonzi, L. Riesgo, M. Tomás, L. A. Lõpez, J. Am. Chem. Soc. 2011, 133, 18138.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 18138
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    • Although it is generally accepted that metal-bound nitrenes are involved in the copper/(N-(p-toluenesulfonyl)imino)phenyliodinane (PhI=NTs) aziridination reaction of alkenes, the nature of the reactive intermediate is still a controversial subject. For a theoretical study, see
    • Although it is generally accepted that metal-bound nitrenes are involved in the copper/(N-(p-toluenesulfonyl)imino)phenyliodinane (PhI=NTs) aziridination reaction of alkenes, the nature of the reactive intermediate is still a controversial subject. For a theoretical study, see:, P. Brandt, M. J. Södergren, P. G. Andersson, P.-O. Norrby, J. Am. Chem. Soc. 2000, 122, 8013.
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    • For a theoretical study on the aziridinylcarbene-azetine rearrangement, see
    • For a theoretical study on the aziridinylcarbene-azetine rearrangement, see:, C. Mück-Lichtenfeld, J. Org. Chem. 2000, 65, 1366.
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    • For a Review of aziridine ring-opening reactions via C-C and C-N bond breaking, see
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.