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Volumn 4, Issue 1, 2012, Pages 123-128

Microwave-Assisted Meyer-Schuster Rearrangement of Propargylic Alcohols Catalyzed by the Oxovanadate Complex [V(O)Cl(OEt) 2]

Author keywords

Alcohols; Enals; Microwave chemistry; Sigmatropic rearrangement; Vanadium

Indexed keywords

ALKYNOLS; CATALYTIC AMOUNTS; ENALS; MEYER-SCHUSTER REARRANGEMENT; MICROWAVE CHEMISTRY; MICROWAVE-ASSISTED; OXOVANADIUM; PROPARGYLIC ALCOHOLS; SIGMATROPIC REARRANGEMENTS; UNSATURATED CARBONYL COMPOUNDS;

EID: 84859852043     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201100239     Document Type: Article
Times cited : (31)

References (95)
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    • A protocol for the selective Meyer-Schuster rearrangement of propargylic alcohols using boronic acids as catalysts under mild conditions has been recently disclosed
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    • Note
    • Application of metal-catalyzed Meyer-Schuster rearrangements to the synthesis of (S)-α-ionone and prostaglandins has also been described recently:
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    • The mechanism of the isomerization of 2-methyl-3-butyn-2-ol into 3-methyl-2-butenal, catalyzed by an oxotitanium complex, has been previously investigated by synthesizing several compounds that model the postulated metal-oxo-propargyloxo intermediate.
    • The mechanism of the isomerization of 2-methyl-3-butyn-2-ol into 3-methyl-2-butenal, catalyzed by an oxotitanium complex, has been previously investigated by synthesizing several compounds that model the postulated metal-oxo-propargyloxo intermediate. C. Y. Lorber, M.-T. Youinou, J. Kress, J. A. Osborn, Polyhedron 2000, 19, 1693-1698.
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    • The basis of this reaction is a [3,3]-sigmatropic transposition of the metal-oxo intermediate. Similar reactions are also known for allylic alcohols using molybdenum, vanadium, or rhenium catalysts.
    • The basis of this reaction is a [3, 3]-sigmatropic transposition of the metal-oxo intermediate. Similar reactions are also known for allylic alcohols using molybdenum, vanadium, or rhenium catalysts.
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    • Note
    • 1)] is involved in the [3, 3]-sigmatropic rearrangement: see reference [16a];
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    • Introduction of a Lewis acid cocatalyst able to coordinate to the C≡C bond of propargylic alcohol is also known to favor the key [3,3]-sigmatropic rearrangement step
    • Introduction of a Lewis acid cocatalyst able to coordinate to the C≡C bond of propargylic alcohol is also known to favor the key [3, 3]-sigmatropic rearrangement step: M. Egi, Y. Yamaguchi, N. Fujiwara, S. Akai, Org. Lett. 2008, 10, 1867-1870.
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    • see also reference [15].
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    • 2] has also been described: see reference[12].
    • 2] has also been described: see reference[12].
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    • The use of lower temperatures and/or catalyst loadings slowed down the reaction considerably; as an example, by using 1mol% of complex 2 under MW irradiation (300W) at 80°C, 3,3-diphenylpropenal was formed in only 80% GC yield after 1h.
    • The use of lower temperatures and/or catalyst loadings slowed down the reaction considerably; as an example, by using 1mol% of complex 2 under MW irradiation (300W) at 80°C, 3, 3-diphenylpropenal was formed in only 80% GC yield after 1h.
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    • 3]: see reference [21g].
    • 3]: see reference [21g].
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    • Such an E selectivity with secondary alkynols has been rarely observed using oxo complexes as catalysts: see reference [16a]. However, several examples of stereoselective non-oxo catalytic systems are known: see, for example, references [16b,c] and
    • Such an E selectivity with secondary alkynols has been rarely observed using oxo complexes as catalysts: see reference [16a]. However, several examples of stereoselective non-oxo catalytic systems are known: see, for example, references [16b, c] and
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    • Note
    • For a recent review article and a book on the chemistry of these species, see:
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    • 3C≡CLi, generated insitu from commercially available 2-bromo-3,3,3-trifluoropropene and lithium diisopropylamide, to the corresponding carbonyl compound. See, for example:
    • 3C≡CLi, generated insitu from commercially available 2-bromo-3, 3, 3-trifluoropropene and lithium diisopropylamide, to the corresponding carbonyl compound. See, for example:
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    • 3-containing secondary propargylic alcohols into enones were described recently
    • 3-containing secondary propargylic alcohols into enones were described recently: Y. Watanabe, T. Yamazaki, J. Org. Chem. 2011, 76, 1957-1960.
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    • Note
    • 3)], and AgOTf has been described to date in the literature: see reference [19b].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.