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Volumn 14, Issue 2, 2012, Pages 429-431

Alkylative ring opening of N -methylaziridinium ions and a formal synthesis of tyroscherin

Author keywords

[No Author keywords available]

Indexed keywords

ADRENALIN; AZIRIDINE DERIVATIVE; DRUG DERIVATIVE; FATTY ALCOHOL; ION; TYROSCHERIN;

EID: 84862973426     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202683k     Document Type: Article
Times cited : (33)

References (35)
  • 11
    • 77649239382 scopus 로고    scopus 로고
    • Lu, P. Tetrahedron 2010, 66, 2549
    • (2010) Tetrahedron , vol.66 , pp. 2549
    • Lu, P.1
  • 22
    • 0344153361 scopus 로고    scopus 로고
    • references cited therein
    • Lee, W. K.; Ha, H.-J. Aldrichimica Acta 2003, 36, 57 and references cited therein
    • (2003) Aldrichimica Acta , vol.36 , pp. 57
    • Lee, W.K.1    Ha, H.-J.2
  • 26
    • 52649129762 scopus 로고    scopus 로고
    • The N -methyl group and the substituent at C-2 are in a cis relationship. We observed correlation signals in NOESY spectra between the N -methyl and methylene protons bearing OMe in 2A
    • Kim, Y.; Ha, H.-J.; Yun, S. Y.; Lee, W. K. Chem. Commun. 2008, 4363. The N -methyl group and the substituent at C-2 are in a cis relationship. We observed correlation signals in NOESY spectra between the N -methyl and methylene protons bearing OMe in 2A
    • (2008) Chem. Commun. , pp. 4363
    • Kim, Y.1    Ha, H.-J.2    Yun, S.Y.3    Lee, W.K.4
  • 29
    • 4143102531 scopus 로고    scopus 로고
    • When the aziridinium ion is formed the ring becomes sufficiently reactive to be attacked by the carbon nucleophile as shown in the CuOTf catalyzed alkynylation of activated aziridines reported in the literature. Due to the low solubility of the aziridinium ion at 0 °C, there is a limitation to the solvent to be used. Among them dioxane was the best for most reactions
    • When the aziridinium ion is formed the ring becomes sufficiently reactive to be attacked by the carbon nucleophile as shown in the CuOTf catalyzed alkynylation of activated aziridines reported in the literature. Ding, C.-H.; Dai, L.-X.; Hou, X-.L. Synlett 2004, 1691. Due to the low solubility of the aziridinium ion at 0 °C, there is a limitation to the solvent to be used. Among them dioxane was the best for most reactions
    • (2004) Synlett , pp. 1691
    • Ding, C.-H.1    Dai, L.-X.2    Hou, X.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.