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Volumn 10, Issue 2, 2004, Pages 484-493

Evidence That Protons Can Be the Active Catalysts in Lewis Acid Mediated Hetero-Michael Addition Reactions

Author keywords

Br nsted acids; Enones; Hydrolysis; Lewis acids; Michael addition

Indexed keywords

CATALYSIS; CATALYSTS; HYDROLYSIS; KETONES; NITROGEN; ORGANIC SOLVENTS; OXYGEN; PROTONS; SULFUR;

EID: 0842349047     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305407     Document Type: Article
Times cited : (313)

References (88)
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    • note
    • See also Supporting Information for kinetic data.
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    • note
    • 2 were preferred solvents due to better solubility of Lewis acid catalysts and faster reactions in most cases.
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    • note
    • CCDC-214434 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.hmtl (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or email: deposit@ccdc.cam.ac. uk).
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    • note
    • 2O (see Experimental Section).
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    • A correlation between catalytic activity and hydrolysis constants and water exchange rate constants has been established for reactions in water, see: S. Kobayashi, S. Nagayama, T. Busujima, J. Am. Chem. Soc. 1998, 120, 8287-8288.
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    • note
    • Due to the wide signal separation, the extent of protonation can even be assessed in the presence of paramagnetic metal ions which cause considerable line broadening.
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    • note
    • 3CN, 12 h).
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    • note
    • 3CN).
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    • note
    • 3CN (see Supporting Information).
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    • note
    • II catalysts, see refs [5a, e].
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    • note
    • IV-complexes have also been used. However, the mechanism of this reaction is not clear (see ref [13d]).
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    • b) J.-Q. Yu, M. J. Gaunt, J. B. Spencer, J. Org. Chem. 2002, 67, 4627-4629]. This is confirmed by the observation that the isomerisation of cis-β-methylstyrene to the trans-isomer is not inhibited by the addition of the non-coordinating ligand 2,6-di-tert-butylpyridine.
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    • note
    • Most aza- and oxa-Michael addition reactions described in this report were reversible.
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    • note
    • 2H coupling.
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    • note
    • It is conceivable that one of these species is an oxazine derivative, which can be formed in acid-catalysed Ritter reactions, see ref. [24]


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.