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Volumn 64, Issue 29, 2008, Pages 6988-6996

Lewis acid-catalyzed Meyer-Schuster reactions: methodology for the olefination of aldehydes and ketones

Author keywords

Aldehyde; Ethoxyacetylene; Ketone; Meyer Schuster; Olefination; Scandium(III) triflate

Indexed keywords

ALDEHYDE DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; SCANDIUM;

EID: 44949179912     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.030     Document Type: Article
Times cited : (59)

References (69)
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    • For seminal examples illustrating this concept, see:
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    • Examples of Meyer-Schuster reactions of ethoxyalkynyl carbinols using hard Lewis or protic acids:
    • Examples of Meyer-Schuster reactions of ethoxyalkynyl carbinols using hard Lewis or protic acids:
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    • The combination of an electron-rich π-system and soft Lewis acid catalyst has also been used in cycloisomerization reactions:
    • The combination of an electron-rich π-system and soft Lewis acid catalyst has also been used in cycloisomerization reactions:. Sun J., Conley M.P., Zhang L., and Kozmin S.A. J. Am. Chem. Soc. 128 (2006) 9705-9710
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    • Because the 1,3-hydroxy shift is not concerted and there is ample opportunity for the hydroxy to exchange with water in the reaction medium, the Meyer-Schuster reaction is not a true rearrangement. For mechanistic investigations of the Meyer-Schuster reaction, see:
    • Because the 1,3-hydroxy shift is not concerted and there is ample opportunity for the hydroxy to exchange with water in the reaction medium, the Meyer-Schuster reaction is not a true rearrangement. For mechanistic investigations of the Meyer-Schuster reaction, see:
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    • note
    • The question as to what reaction pathway(s) leading from the propargyl acetate to the α,β-unsaturated ketone is catalyzed by cationic gold salts remains open. For further discussion, see Ref. 20f.
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    • Related reactions of propargyl acetates:
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    • For example, it was our inability to achieve Horner-Wadsworth-Emmons olefination reactions on either menthone (cf. 1h→3h) or menthone derivatives that initially prompted our interest in Meyer-Schuster reaction methodology. For more information on the steric congestion of menthone derivatives, see:
    • For example, it was our inability to achieve Horner-Wadsworth-Emmons olefination reactions on either menthone (cf. 1h→3h) or menthone derivatives that initially prompted our interest in Meyer-Schuster reaction methodology. For more information on the steric congestion of menthone derivatives, see:. Dudley G.B., Engel D.A., Ghiviriga I., Lam H., Poon K.W.C., and Singletary J.A. Org. Lett. 9 (2007) 2839-2842
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    • note
    • The Meyer-Schuster reactions of tertiary alcohols 2 may take a different course. Further investigations are planned and will be communicated in due course.
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    • note
    • Reactions conducted with less than a full equivalent of propanol were slow and inefficient, and are omitted from Table 5.
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    • For full characterization, see:
    • For full characterization, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.