期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 52, 页码 16815-16822出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201202263
关键词
cyclisation; density functional theory; domino reactions; Lewis acids; reaction mechanisms
资金
- French Agence Nationale de la Recherche [ANR07-CP2D, CASAL-04-01]
- University of Nice - Sophia Antipolis
- CNRS
Cycloisomerisation of polyenes such as diethyl geranylprenylmalonate [(E)-1a], diethyl geranylphenylmalonate [(E)-2a] and diethyl cinnamylgeranylmalonate [(E,E)-3a] catalysed by bismuth triflate was studied from experimental and theoretical viewpoints. Several intermediates were isolated and characterised, and calculated transition-state structures are proposed for the three reactions. The diastereoselectivity observed during the reaction of (E)- or (Z)-2a in favour of the formation of trans-fused bicyclic products is discussed in detail. The nature of the active catalytic species derived from bismuth triflate was also investigated, and the formation of a hybrid Lewis acid/Bronsted acid catalyst with water molecules is proposed, supported by experimental and theoretical data.
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