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Volumn 15, Issue 17, 2004, Pages 2599-2602

α-Hydroxy ketones in high enantiomeric purity from asymmetric oxidation of enol phosphates with (salen) manganese(III) complex

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; MANGANESE DERIVATIVE; PHOSPHATE;

EID: 4444362795     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.07.035     Document Type: Article
Times cited : (18)

References (43)
  • 9
    • 0000011522 scopus 로고    scopus 로고
    • E.N. Jacobsen A. Pfaltz H. Yamamoto Springer Berlin
    • D. Enders, and K. Breuer E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis Vol. 2 1999 Springer Berlin 1093 1102
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 1093-1102
    • Enders, D.1    Breuer, K.2
  • 30
    • 85077897850 scopus 로고
    • Enol phosphates 2a-h were prepared from the corresponding ketones by the action of dialkylphosphorochloridate, according to reported procedure: T. Hayashi, T. Fujiwa, Y. Okamoto, Y. Katsuro, and M. Kumada Synthesis 1981 1001
    • (1981) Synthesis , pp. 1001
    • Hayashi, T.1    Fujiwa, T.2    Okamoto, Y.3    Katsuro, Y.4    Kumada, M.5
  • 34
    • 4444362053 scopus 로고    scopus 로고
    • note
    • 3 was added, the organic layer was separated, washed with water, and dried. After removal of the solvent, the residue was subjected to silica gel column chromatography with hexane-ethyl acetate (3:1 v/v) as the eluent, to afford pure, optically active α-hydroxy ketones 4
  • 35
    • 4444263657 scopus 로고    scopus 로고
    • note
    • +) 213.09155. Found 213.09102
  • 36
    • 4444247889 scopus 로고    scopus 로고
    • note
    • HPLC conditions: For entries 1, 2, 5, 8: Chiralcel OD, 5% i-PrOH in hexane, 0.4 mL/min; For entry 3: Chiralcel OD, 4% i-PrOH in hexane, 0.4 mL/min; For entry 4: Chiralcel OD, 3% i-PrOH in hexane, 0.3 mL/min; For entry 6: Chiralcel OD, 0.25% i-PrOH in hexane, 0.3 mL/min; For entry 7: Chiralcel OD, 0.5% i-PrOH in hexane, 0.5 mL/min. All runs were carried out at room temperature
  • 37
    • 4444305678 scopus 로고    scopus 로고
    • note
    • Racemic α-hydroxy ketones 4 were obtained by MCPBA acid oxidation of the corresponding enol phosphates 2a-h followed by the hydrolysis of resulted epoxides 3a-h with 25% of trifluoroacetic acid in ether solution at 5-10°C


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.