Lewis super-acid catalyzed cyclizations: a new route to fragrance compounds |
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Authors: | Coulombel Lydie Grau Fanny Weïwer Michel Favier Isabelle Chaminade Xavier Heumann Andreas Bayón J Carles Aguirre Pedro A Duñach Elisabet |
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Institution: | 1. Laboratoire de Chimie des Molécules Bioactives et des Ar?mes, Université de Nice‐Sophia Antipolis, CNRS, UMR 6001, Institut de Chimie de Nice, Parc Valrose, F‐06108 Nice Cedex 2, (phone: +33?492?076?142;2. fax: +33?492?076?151);3. Université Paul Cézanne, UMR CNRS 6180 ‘Chirotechnologies et Biocatalyse' Faculté Saint‐Jér?me, F‐13397 Marseille Cedex 20;4. Departament de Quimica, Universitat Autònoma de Barcelona, Bellaterra, E‐08193 Barcelona |
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Abstract: | This review deals with the application of Lewis super acids such as Al(III), In(III), and Sn(IV) triflates and triflimidates as catalysts in the synthesis of fragrance materials. Novel catalytic reactions involving C-C and C-heteroatom bond-forming reactions, as well as cycloisomerization processes are presented. In particular, Sn(IV) and Al(III) triflates were employed as catalysts in the selective cyclization of unsaturated alcohols to cyclic ethers, as well as in the cyclization of unsaturated carboxylic acids to lactones. The addition of thiols and thioacids to non-activated olefins, both in intra- and intermolecular versions, was efficiently catalyzed by In(III) derivatives. Sn(IV) Triflimidates catalyzed the cycloisomerization of highly substituted 1,6-dienes to gem-dimethyl-substituted cyclohexanes bearing an isopropylidene substituent. The hydroformylation of these unsaturated substrates, catalyzed by a Rh(I) complex with a bulky phosphite ligand, selectively afforded the corresponding linear aldehydes. The olfactory evaluation of selected heterocycles, carbocycles, and aldehydes synthesized is also discussed. |
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Keywords: | Lewis super acids Metal triflates Cycloisomerization Catalysis |
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