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Volumn 70, Issue 11, 2005, Pages 4272-4278

Efficient allylation of aldehydes promoted by carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; ORGANIC SOLVENTS; REACTION KINETICS;

EID: 19544363411     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050186q     Document Type: Article
Times cited : (49)

References (54)
  • 1
    • 0004063249 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim, Germany
    • For recent reviews, see: (a) Davies, A. G. Organotin Chemistry; Wiley-VCH: Weinheim, Germany, 2004.
    • (2004) Organotin Chemistry
    • Davies, A.G.1
  • 9
    • 0033583196 scopus 로고    scopus 로고
    • Brønsted acid and Lewis acids (reported in recent years), see: (a) Loh, T.-P.; Xu, J. Tetrahedron Lett. 1999, 40, 2431-2434.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2431-2434
    • Loh, T.-P.1    Xu, J.2
  • 31
    • 19544372133 scopus 로고    scopus 로고
    • note
    • Two reviewers suggested that an additional factor of the allylation might be the solubility of the acid in acetonitrile.
  • 32
    • 19544378890 scopus 로고    scopus 로고
    • note
    • Boc-D-phenylalaninal was used freshly after its preparation or it would racemize in a period of time.
  • 36
    • 19544382744 scopus 로고    scopus 로고
    • note
    • 2H.
  • 47
    • 19544392741 scopus 로고    scopus 로고
    • note
    • (b) If benzaldehyde was added after the mixture of crotyltributyltin and maleic acid in acetonitrile was stirred for 3 h, no desired product was obtained. TLC indicated that crotyltributyltin was decomposed.
  • 48
    • 19544382229 scopus 로고    scopus 로고
    • note
    • (a) The mixture of the pure compound 7 a (1.0 equiv), benzaldehyde (1.0 equiv), and trifluoroacetic acid (1.0 equiv) was stirred for 1.0 h in acetonitrile. And no 6a was produced,
  • 49
    • 19544393780 scopus 로고    scopus 로고
    • note
    • 3 (0.5 equiv), and trifluoroacetic acid (0.5 equiv) was stirred for 1.0 h in acetonitrile.
  • 50
    • 19544382567 scopus 로고    scopus 로고
    • note
    • 1H NMR study of crotylation of benzaldehyde shows that adducts 6 and 7 are produced simultaneously.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.