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DOI: 10.1055/s-0034-1379712
Chemoselective Reduction of α,β-Unsaturated Aldehydes with AuNPore
Publication History
Publication Date:
15 December 2014 (online)

Significance
Nanoporous gold (AuNPore) catalyzed the 1,2-reduction of α,β-unsaturated aldehydes 1 with triethylsilane. The reduction was carried out in the presence of water and triethylamine to give the corresponding allyl alcohols 2 in 42–78% yield with 82:18 to 100:0 (2/3) chemoselectivity.
Comment
Previously, the authors reported the AuNPore-catalyzed chemoselective reduction of imines with dimethylphenylsilane (Org. Lett. 2014, 16, 2558). In the reduction of cinnamyl aldehyde, the catalytic activity of AuNPore was superior to that of Au30Ag70 alloy, homogeneous AuCl(Ph3P)/Bu3P, and AuCl/IPr·HCl. ICP-MS analysis showed that no gold content was leached from the catalyst during the reaction.
