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Volumn 11, Issue 7, 2009, Pages 1539-1542

Oxidation of oximes to nitrile oxides with hypervalent iodine reagents

Author keywords

[No Author keywords available]

Indexed keywords

IODINATED HYDROCARBON; NITRILE; OXIDE; OXIME;

EID: 64349107671     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900194v     Document Type: Article
Times cited : (202)

References (40)
  • 2
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    • Reviews: a, Mulzer, J, Altenbach, H. J, Braun, M, Krohn, K, Reissig, H. U, Eds, VCH: Weinheim
    • Reviews: (a) Mulzer, J. In Organic Synthesis Highlights; Mulzer, J., Altenbach, H. J., Braun, M., Krohn, K., Reissig, H. U., Eds.; VCH: Weinheim, 1990; Vol. I, p 77.
    • (1990) Organic Synthesis Highlights , vol.1 , pp. 77
    • Mulzer, J.1
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    • Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247. See especially pp 12255-12259.
    • (b) Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247. See especially pp 12255-12259.
  • 14
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    • and references cited therein
    • Wipf, P.; Spencer, S. R. J. Am. Chem. Soc. 2005, 127, 225, and references cited therein.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 225
    • Wipf, P.1    Spencer, S.R.2
  • 18
    • 0000892411 scopus 로고    scopus 로고
    • Fluoroalcohol solvents are particularly efficacious in DIB-mediated oxidations: Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857.
    • Fluoroalcohol solvents are particularly efficacious in DIB-mediated oxidations: Kita, Y.; Takada, T.; Gyoten, M.; Tohma, H.; Zenk, M. H.; Eichhorn, J. J. Org. Chem. 1996, 61, 5857.
  • 19
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    • See also refs 1d and 3
    • See also refs 1d and 3.
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    • See also refs 1a and 1b
    • See also refs 1a and 1b.
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    • Prepared from 1-[2-(1,3-dioxolan-2-yl)ethyl]-2,5-cyclohexadiene-1- carboxylic acid (a) Chuang, C. P.; Gallucci, J. C; Hart, D. J. J. Org. Chem. 1988, 53, 3218.
    • Prepared from 1-[2-(1,3-dioxolan-2-yl)ethyl]-2,5-cyclohexadiene-1- carboxylic acid (a) Chuang, C. P.; Gallucci, J. C; Hart, D. J. J. Org. Chem. 1988, 53, 3218.
  • 33
    • 0000188389 scopus 로고    scopus 로고
    • 2. Interestingly, the TMS group remained in place throughout the sequence. For details, see the Supporting Information.
    • 2. Interestingly, the TMS group remained in place throughout the sequence. For details, see the Supporting Information.
  • 34
    • 64349115138 scopus 로고    scopus 로고
    • Prepared from ethyl 1-[2-(1,3-dioxolan-2-yl)ethyl]-2- oxocyclohexanecarboxylate (Singh, K. P.; Mandell, L. Chem. Ber. 1963, 96, 2485.) as described in the Supporting Information.
    • Prepared from ethyl 1-[2-(1,3-dioxolan-2-yl)ethyl]-2- oxocyclohexanecarboxylate (Singh, K. P.; Mandell, L. Chem. Ber. 1963, 96, 2485.) as described in the Supporting Information.
  • 35
    • 64349102816 scopus 로고    scopus 로고
    • The oxidative cyclization of 9 was more efficient when run in the significantly costlier HFIP as the solvent (85% chromatographed yield). Details are provided as Supporting Information.
    • The oxidative cyclization of 9 was more efficient when run in the significantly costlier HFIP as the solvent (85% chromatographed yield). Details are provided as Supporting Information.
  • 36
    • 64349091812 scopus 로고    scopus 로고
    • The resonances of the axial proton on the methylene adjacent to the oximino group (ca. 1.8 ppm) and of the methyl-bearing methine (ca. 1.50 ppm) overlap with those of other ring protons, preventing the accurate determination of coupling constants and, hence, of the configuration
    • The resonances of the axial proton on the methylene adjacent to the oximino group (ca. 1.8 ppm) and of the methyl-bearing methine (ca. 1.50 ppm) overlap with those of other ring protons, preventing the accurate determination of coupling constants and, hence, of the configuration.
  • 37
    • 64349113268 scopus 로고    scopus 로고
    • Relevant data are provided as Supporting Information
    • Relevant data are provided as Supporting Information.
  • 40
    • 64349101144 scopus 로고    scopus 로고
    • The preparation of 18 is detailed in the Supporting Information.
    • The preparation of 18 is detailed in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.