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Lewis Super-Acid Catalyzed Cyclizations: A New Route to Fragrance Compounds

✍ Scribed by Lydie Coulombel; Fanny Grau; Michel Weïwer; Isabelle Favier; Xavier Chaminade; Andreas Heumann; J. Carles Bayón; Pedro A. Aguirre; Elisabet Duñach


Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
310 KB
Volume
5
Category
Article
ISSN
1612-1872

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✦ Synopsis


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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