Synthesis, Table of Contents Synthesis 2015; 47(02): 272-288DOI: 10.1055/s-0034-1379254 paper © Georg Thieme Verlag Stuttgart · New YorkA Practical, Enantioselective Synthesis of the Fragrances Canthoxal and Silvial®, and Evaluation of Their Olfactory Activity Authors Author Affiliations Valentina Beghetto* a Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Dorsoduro 2137, 30123 Venezia, Italy Alberto Scrivanti a Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Dorsoduro 2137, 30123 Venezia, Italy Matteo Bertoldini a Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Dorsoduro 2137, 30123 Venezia, Italy Manuela Aversa b Consorzio Interuniversitario CIRCC, UdR di Venezia, Via C. Ulpiani 27, 70126 Bari, Italy Fax: +39(041)2348517 Email: beghetto@unive.it Aurora Zancanaro a Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Dorsoduro 2137, 30123 Venezia, Italy Ugo Matteoli a Dipartimento di Scienze Molecolari e Nanosistemi, Università Ca’ Foscari Venezia, Dorsoduro 2137, 30123 Venezia, Italy Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) 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. Key words Key wordsfragrance synthesis - asymmetric hydrogenation - ruthenium - canthoxal - Silvial® Full Text References References Selected references: 1a Kraft P, Mannschreck A. J. Chem. Educ. 2010; 87: 598 1b Bentley R. Chem. Rev. 2006; 106: 4099 1c Abate A, Brenna E, Fuganti C, Gatti FG, Serra S. Chem. Biodiversity 2004; 1: 1888 1d Brenna E, Fuganti C, Serra S. Tetrahedron: Asymmetry 2003; 14: 1 1e Kraft P, Fráter G. Chirality 2001; 13: 388 1f Kraft P, Bajgrowicz JA, Denis C, Fráter G. Angew. Chem. Int. Ed. 2000; 39: 2980 2 Chapuis C. Helv. Chim. Acta 2012; 95: 1479 Selected references: 3a Schwartz S, Berding V, Matthies M. Chemosphere 2000; 41: 671 3b Peck AM, Hornbuckle KC. Atmos. 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