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Volumn , Issue 11, 2002, Pages 1112-1113

Asymmetric 1,3-dipolar cycloaddition of nitrile oxides generated in situ by direct oxidation of aldoximes

Author keywords

[No Author keywords available]

Indexed keywords

ALDOXIME; ALLYL ALCOHOL; HYPOCHLORITE; ISOXAZOLINE DERIVATIVE; NITRILE; TARTARIC ACID DERIVATIVE; TERT BUTYLHYPOCHLORITE; UNCLASSIFIED DRUG;

EID: 0037027697     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.1112     Document Type: Article
Times cited : (43)

References (21)
  • 3
    • 0012929677 scopus 로고    scopus 로고
    • ed. by S. Kobayashi and K. A. Jørgensen, Wiley-VCH, Weinheim, Chap. 6.
    • c) K. V. Gothelf, in "Cycloaddition Reactions in Organic Synthesis," ed. by S. Kobayashi and K. A. Jørgensen, Wiley-VCH, Weinheim (2002), Chap. 6.
    • (2002) Cycloaddition Reactions in Organic Synthesis
    • Gothelf, K.V.1
  • 4
    • 0012931076 scopus 로고    scopus 로고
    • ed. by S. Kobayashi and K. A. Jørgensen, Wiley-VCH, Weinheim, Chap. 7
    • d) S. Kanemasa, in "Cycloaddition Reactions in Organic Synthesis," ed. by S. Kobayashi and K. A. Jørgensen, Wiley-VCH, Weinheim (2002), Chap. 7.
    • (2002) Cycloaddition Reactions in Organic Synthesis
    • Kanemasa, S.1
  • 17
    • 0012976174 scopus 로고    scopus 로고
    • note
    • The reason for low enantioselectivities in the case of N-halosuccinimide is not clear. The coordination of N-halosuccinimide and/or produced succinimide to zinc in 4 might change the ideal structure of the intermediate to lower the enatioselectivities.
  • 19
    • 0012934975 scopus 로고    scopus 로고
    • note
    • If the intermediate 3 was produced completely by the reaction of alkylzinc moiety in 2 with aldoxime, the kind of alkyl group in dialkylzinc would not influence the chemical yield and enantio-selectivity. The fact that those were altered depending on the used dialkylzinc might indicate the incompletion of the reaction of methyl- and ethylzinc moiety in 2 with aldoxime.
  • 20
    • 0013011934 scopus 로고    scopus 로고
    • Recently we found a concentration effect for the 1,3-dipolar cycloaddition of a nitrone to give the corresponding isoxazolidines with higher enantioselectivity in higher chemical yield: D. Xia, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 2002, 302.
    • Chem. Lett. , vol.2002 , pp. 302
    • Xia, D.1    Ukaji, Y.2    Fujinami, S.3    Inomata, K.4
  • 21
    • 0012928203 scopus 로고    scopus 로고
    • note
    • 3. Purification by column chromatography on silica gel afforded 2-isoxazoline 5a (227 mg, 76%) in 93% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.