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Volumn 42, Issue 7, 2003, Pages 828-831

Organic-catalyst-mediated cyclopropanation reaction

Author keywords

Asymmetric synthesis; Cyclopropanation; Diastereoselectivity; Organocatalysis; Ylides

Indexed keywords

AMMONIUM COMPOUNDS; ELECTRONS; OLEFINS; STOICHIOMETRY;

EID: 0037450150     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390222     Document Type: Article
Times cited : (179)

References (28)
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    • note
    • 13C NMR spectroscopy, high-resolution mass spectrometry and infrared spectroscopy.
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    • trans-Stereochemistry was confirmed in 3a by hydrolysis of the tert-butyl ester and comparison with an authentic sample, and in 3e by X-ray crystal-structure analysis.
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    • note
    • We also found that using quinuclidine in place of DABCO produced 3a in similar yield.
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    • note
    • Phenacyl chloride did not react with the more hindered chiral amine.
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    • note
    • See supporting information for details chiral HPLC analysis.
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    • No cyclopropane formation was observed when the reaction was carried out with styrene instead of the electron-deficient alkenes which suggests that the reaction does not proceed through a carbene mechanism.
  • 26
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    • note
    • In the case of methyl vinyl ketone, 3.0 equiv was used because of its volatility. In the other cases only 1.5 equiv of the alkene was used.
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    • For an overview of organocatalysis, see: P. I. Dalko, L. Moisan, Angew. Chem. 2001, 113, 3840; Angew. Chem. Int. Ed. 2001, 40, 3726.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.