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Synfacts 2015; 11(1): 0098
DOI: 10.1055/s-0034-1379712
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Chemoselective Reduction of α,β-Unsaturated Aldehydes with AuNPore

Contributor(s):
Yasuhiro Uozumi
,
Fumie Sakurai
Takale BS, Wang S, Zhang X, Feng X, Yu X, Jin T, Bao M, * Yamamoto Y. * Dalian University of Technology, P. R. of China and Tohoku University, Sendai, Japan
Chemoselective Reduction of α,β-Unsaturated Aldehydes Using An Unsupported Nanoporous Gold Catalyst.

Chem. Commun. 2014;
50: 14401-14404
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

nanoporous gold - reduction - α,β-unsaturated aldehydes - alcohols

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.


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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.


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