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Volumn 16, Issue 28, 2010, Pages 8248-8250

Rhodium-catalyzed synthesis of γ-pyrones by three consecutive redoxaldol reactions of allylic alcohols with α, β-unsaturated aldehydes

Author keywords

Aldehydes; Aldol reaction; Allylic compounds; Homogeneous catalysis

Indexed keywords

ALDOL REACTIONS; ALLYLIC ALCOHOL; ALLYLIC COMPOUNDS; CATALYZED REACTIONS; HOMOGENEOUS CATALYSIS; RHODIUM-CATALYZED SYNTHESIS; TRIKETONE; TRIMETHYLSILYL; UNSATURATED ALDEHYDES;

EID: 77954855024     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001068     Document Type: Article
Times cited : (17)

References (44)
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    • For examples of Claisen-type reactions, such as a coupling of dianions of 1,3-diketones with acylating agents, see: a) A. Sakakura, H. Watanabe, K. Ishihara, Org. Lett. 2008, 10, 2569-2572;
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    • c) P. J. Wittek, K. B. Hindley, T. M. Harris, J. Org. Chem. 1973, 38, 896-901. For examples of oxidation of the corresponding β-hydroxyketone derivatives, see:
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    • For reviews on catalytic isomerization of allylic alcohols, see : a) R. Uma, C. Crévisy, R. Grée, Chem. Rev. 2003, 103, 27-51;
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    • Uma, R.1    Crévisy, C.2    Grée, R.3
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    • (Eds.: P. Andersson, I. Munslow), Wiley-VCH, Weinheim
    • For recent reviews of transition metal-catalyzed reductive aldol reaction, see: a) S. Garner, S. B. Han, M. J. Krische in Modern Reductions (Eds.: P. Andersson, I. Munslow), Wiley-VCH, Weinheim, 2008, 387-408;
    • (2008) Modern Reductions , pp. 387-408
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    • 2O instead of TMSOTf to afford 4d and 8c, respectively. (Figure Presented)
    • 2O instead of TMSOTf to afford 4d and 8c, respectively. (Figure Presented)
  • 38
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    • It should be noted that in case of an allylic alcohol with no substituent on the a position, the exo-enolate D' generated might undergo isomerization to the more stable endo-enolate I, however, this isomerization did not take place as a major reaction pathway. (Figure Presented)
    • It should be noted that in case of an allylic alcohol with no substituent on the a position, the exo-enolate D' generated might undergo isomerization to the more stable endo-enolate I, however, this isomerization did not take place as a major reaction pathway. (Figure Presented)
  • 39
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    • 1-Alkyl-substituted allylic alcohols gave isomerized ketones only. It is likely the reactivity of the enolates is lower.
    • 1-Alkyl-substituted allylic alcohols gave isomerized ketones only. It is likely the reactivity of the enolates is lower.
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    • For representative examples of γ-pyrone synthesis, see: a) Y. R. Lee, J. Y. Suk, B. S. Kim, Org. Lett. 2000, 2, 1387-1389;
    • (2000) Org. Lett. , vol.2 , pp. 1387-1389
    • Lee, Y.R.1    Suk, J.Y.2    Kim, B.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.