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Volumn 132, Issue 26, 2010, Pages 8810-8812

An enantioselective claisen rearrangement catalyzed by N-heterocyclic carbenes

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION PARAMETER; ADDED BASE; ANNULATION REACTIONS; AZOLIUM SALTS; CATALYTIC SYSTEM; CATALYTICALLY ACTIVE SPECIES; CATALYZED REACTIONS; CLAISEN REARRANGEMENT; COUNTERIONS; DETAILED KINETICS; DIHYDROPYRANONES; ENANTIOSELECTIVE; KOJIC ACID; MECHANISTIC PATHWAYS; N-HETEROCYCLIC CARBENES; RATE LAWS; RATE-LIMITING STEPS; SYNTHETIC UTILITY;

EID: 77954281480     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103631u     Document Type: Article
Times cited : (305)

References (53)
  • 3
    • 37549022166 scopus 로고    scopus 로고
    • Hiersemann, M. and Nubbemeyer, U., Eds. Wiley-VCH: Weinheim, Germany
    • Hiersemann, M. and Nubbemeyer, U., Eds. The Claisen Rearrangment; Wiley-VCH: Weinheim, Germany, 2007.
    • (2007) The Claisen Rearrangment
  • 38
    • 77954291692 scopus 로고    scopus 로고
    • note
    • Imidazolinium salts substituted at the 2-position, which cannot form carbenes, have been employed as catalyzed for aza-Diels Alder reactions. In this case the salts are thought to act as Lewis acids
  • 40
    • 77954605119 scopus 로고    scopus 로고
    • in press (DOI: 10.1039/c003301d)
    • For a recent report on the use of imidazolium salts for acid catalyzed acetylations, see: Myles, L., Gore, R., Spulák, M., Gathergood, N., and Connon, S. J. Green Chem. 2010, in press (DOI: 10.1039/c003301d).
    • (2010) Green Chem.
    • Myles, L.1    Gore, R.2    Spulák, M.3    Gathergood, N.4    Connon, S.J.5
  • 41
    • 0008520232 scopus 로고
    • For an alternative mechanism for the addition of azolium salts to aldehydes, see: Crane, E. J., III and Washabaugh, M. W. Bioorg. Chem. 1991, 19, 351-368
    • (1991) Bioorg. Chem. , vol.19 , pp. 351-368
    • Crane Iii, E.J.1    Washabaugh, M.W.2
  • 43
    • 77954291122 scopus 로고    scopus 로고
    • Townsend has postulated a conjugate addition to an α,β- unsaturated acyl azolium in the biosynthesis of clavulanic acid, see ref 10.
    • Townsend has postulated a conjugate addition to an α,β- unsaturated acyl azolium in the biosynthesis of clavulanic acid, see ref 10.
  • 46
    • 77954298967 scopus 로고    scopus 로고
    • See the Supporting Information for the derivation of this rate law.
    • See the Supporting Information for the derivation of this rate law.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.