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Volumn 12, Issue 15, 2010, Pages 3376-3379

Direct carbon-carbon bond formation via soft enolization: A biomimetic asymmetric mannich reaction of phenylacetate thioesters

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBON; CINCHONA ALKALOID; ESTER; PHENYLACETIC ACID DERIVATIVE; SULFUR DERIVATIVE;

EID: 77955161875     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101152b     Document Type: Article
Times cited : (51)

References (53)
  • 1
    • 33845377839 scopus 로고
    • For pioneering examples of soft enolization, see: Rathke, M. W.; Cowan, P. J. J. Org. Chem. 1985, 50, 2622-2624
    • (1985) J. Org. Chem. , vol.50 , pp. 2622-2624
    • Rathke, M.W.1    Cowan, P.J.2
  • 11
    • 0035881923 scopus 로고    scopus 로고
    • The effect of hydrogen bonding on thioester acidity has been shown for acetyl-CoA dehydrogenase. See: Rudik, I.; Thorpe, C. Arch. Biochem. Biophys. 2001, 392, 341-348
    • (2001) Arch. Biochem. Biophys. , vol.392 , pp. 341-348
    • Rudik, I.1    Thorpe, C.2
  • 12
    • 77955170274 scopus 로고    scopus 로고
    • For accounts of proximity accelerated intramolecular transformations in general, see
    • For accounts of proximity accelerated intramolecular transformations in general, see
  • 20
    • 77955129690 scopus 로고    scopus 로고
    • In other studies thioesters were shown to be well-suited to soft enolization, compared to oxoesters and amides (see ref 2d)
    • In other studies thioesters were shown to be well-suited to soft enolization, compared to oxoesters and amides (see ref 2d).
  • 21
    • 77955136529 scopus 로고    scopus 로고
    • For reviews of organocatalytic Mannich reactions see
    • For reviews of organocatalytic Mannich reactions see
  • 24
    • 77955137745 scopus 로고    scopus 로고
    • For examples of thioesters in organocatalysis, see
    • For examples of thioesters in organocatalysis, see
  • 31
    • 77955129198 scopus 로고    scopus 로고
    • Whether enolate stabilization is the result of a strong hydrogen bond or an ionic bond is uncertain
    • Whether enolate stabilization is the result of a strong hydrogen bond or an ionic bond is uncertain.
  • 45
    • 77955164187 scopus 로고    scopus 로고
    • A similar experiment with the analogous oxoester (phenyl acetic acid phenyl ester) gave only recovered starting material after 36 h
    • A similar experiment with the analogous oxoester (phenyl acetic acid phenyl ester) gave only recovered starting material after 36 h.
  • 51
    • 77955139916 scopus 로고    scopus 로고
    • The lower yields for 20 resulted from incomplete conversion
    • The lower yields for 20 resulted from incomplete conversion.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.