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Synthesis 2010(8): 1325-1333  
DOI: 10.1055/s-0029-1218653
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Efficient Cs2CO3-Catalyzed 1,4-Addition of Me3SiCN to Enones with Water as the Additive

Jingya Yanga,b, Yongbin Shena, Fu-Xue Chen*a
a Department of Applied Chemistry, School of Chemical Engineering & the Environment, Beijing Institute of Technology, 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China
b College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, P. R. of China
Fax: +86(10)68918296; e-Mail: fuxue.chen@bit.edu.cn;
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Publikationsverlauf

Received 25 November 2009
Publikationsdatum:
29. Januar 2010 (online)

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Abstract

A facile and efficient 1,4-addition of Me3SiCN to enones has been achieved with perfect regioselectivity using Cs2CO3 as catalyst. Thus, with 0.5 mol% of Cs2CO3 and 4 equivalents of H2O as the additive excellent yields (81-99%) of β-cyanoketones are obtained within one to five hours. Both aromatic and aliphatic enones are found suitable substrates for this protocol.

Key words

1,4-addition - catalysis - enones - nitriles - regioselectivity

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25

Preliminary studies on asymmetric version of this protocol yielded racemic product using alkali metal salt of l-proline or chiral sodium phosphate as catalysts in the 1,4-addition of Me3SiCN to chalcone (1a) in refluxing dioxane.