Ruthenium complex-catalyzed oxidative cyclization of 4-penten-1-ols

Chemistry Letters

Volumn 32, Issue 1, 2003, Pages 24-25

  Kondo, Teruyuki ^a   Tsunawaki, Fumiaki ^a   Sato, Ryosuke ^a   Ura, Yasuyuki ^a   Wada, Kenji ^a   Mitsudo, Take Aki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,5 DIMETHYL 2 PHENYL 2,3 DIHYDROFURAN; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALLYL ACETATE; CARBON MONOXIDE; FURAN DERIVATIVE; LIGAND; POTASSIUM DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; OXIDATION; QUANTITATIVE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 0037419583     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.24     Document Type: Article

References (24)

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19. 3 could be reduced to a common active Ru(0) species, which can explain the effectiveness of these Ru(II) and Ru(III) catalysts as Ru(0) catalysts for the present oxidative cyclization reaction.
20. The reaction using 1,1-disubstituted 4-hexen-1-ols which have methyl substituents on the terminal olefinic carbon, such as 2-phenyl-5-hepten-2-ol, is quite complicated. The yield of normal oxidative cyclization product, 2,5-dimethyl-5-phenyl-4,5-dihydrofuran, was quite low (>5%), while the oxidative cyclocarbonylation on the phenyl substituent occurred to give unexpected 3-methyl-3-(pent-3-enyl)phthalide in 48% yield. Similar oxidative cyclocarbonylation proceeded quantitatively with 1,1-disubstituted 5-hexen-1-ols. Further studies are apparently required for these reactions.
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24. 4,9 No propyl acetate, a simple hydrogenated product of allyl acetate, was detected by careful GC analysis.