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Synthesis 2015; 47(02): 272-288
DOI: 10.1055/s-0034-1379254
DOI: 10.1055/s-0034-1379254
paper
A Practical, Enantioselective Synthesis of the Fragrances Canthoxal and Silvial®, and Evaluation of Their Olfactory Activity
Further Information
Publication History
Received: 31 July 2014
Accepted after revision: 18 September 2014
Publication Date:
24 October 2014 (online)
Abstract
The fragrances (S)-(+)- and (R)-(–)-canthoxal [(S)-(+)- and (R)-(–)-3-(4-methoxyphenyl)-2-methylpropanal] and (+)- and (–)-Silvial® [(+)- and (–)-3-(4-isobutylphenyl)-2-methylpropanal] have been synthesized in high enantiopurity via a simple four-step strategy starting from the commercially available 4-substituted benzaldehydes. The key synthetic step is the catalytic asymmetric hydrogenation of the appropriate 3-aryl-2-methylacrylic acid which has been carried out employing an in situ prepared ruthenium/axially chiral phosphine catalyst (up to 98% ee). The olfactory activity of the single enantiomers has been evaluated.
Supporting Information
- ffor this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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