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

Jingya Yang, Yongbin Shen, Fu-Xue Chen*

*Department of Applied Chemistry, School of Chemical Engineering & the Environment, Beijing Institute of Technology, No. 5 South Zhongguancun Street, Haidian District, Beijing 100081, P. R. of China, Email: fuxue.chenbit.edu.cn

J. Yang, Y. Shen, F.-X. Chen, Synthesis, 2010, 1325-1333.

DOI: 10.1055/s-0029-1218653

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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 in the presence of H₂O as an additive. β-Cyanoketones are obtained in excellent yields within one to five hours. Both aromatic and aliphatic enones are suitable substrates.

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The Highly Efficient 1,4-Addition of TMSCN to Aromatic Enones Catalyzed by CsF with Water as the Additive

J. Yang, Y. Wang, S. Wu, F.-X. Chen, Synlett, 2009, 3365-3367.

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Key Words

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

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ID: J66-Y2010-0930