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Synthesis 2013; 45(6): 729-733
DOI: 10.1055/s-0032-1318169
DOI: 10.1055/s-0032-1318169
practical synthetic procedures
A Mild PPTS-Catalyzed Acetalization of α,β-Unsaturated Aldehydes: The First Single-Step Protocol towards Benzylic Acetals
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
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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