Synthesis 2013; 45(6): 729-733
DOI: 10.1055/s-0032-1318169
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

A Mild PPTS-Catalyzed Acetalization of α,β-Unsaturated Aldehydes: The First Single-Step Protocol towards Benzylic Acetals

Dietrich Böse
Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf am Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany    Fax: +49(2461)611669   Email: [email protected]
,
Marvin Lübcke
Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf am Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany    Fax: +49(2461)611669   Email: [email protected]
,
Jörg Pietruszka*
Institut für Bioorganische Chemie der Heinrich-Heine-Universität Düsseldorf am Forschungszentrum Jülich, Stetternicher Forst, Geb. 15.8, 52426 Jülich, Germany    Fax: +49(2461)611669   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 20 November 2012

Accepted after revision: 16 January 2013

Publication Date:
08 February 2013 (online)


Abstract

A mild and convenient procedure for the synthesis of highly sensitive benzylic acetals from α,β-unsaturated aldehydes and the corresponding benzylic alcohols is reported. The new method provides a single-step access to these compounds for the first time. The applications of pyridinium p-toluenesulfonate (PPTS) as a very mild Brønsted acid catalyst and 5 Å molecular sieves (MS) as the dehydrating agent were found to be essential. Furthermore, an application of the acetals in the synthesis of 1-functionalized dienes is exemplified.

Supporting Information

 
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