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Vol. 25 No. 5 (2013): Vol 25 Issue 5

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A Mild and Efficient Procedure for Asymmetric Michael Additions of a-Bromochalcone with Cyclohexanone Catalyzed by Different Bases

https://doi.org/10.14233/ajchem.2013.13457
Li-Guo Gao
School of Chemical Engineering, Tianjin University, Tianjin 300072, P.R. China
Dong-Zhi Liu
School of Chemical Engineering, Tianjin University, Tianjin 300072, P.R. China
Wei Li
School of Chemical Engineering, Tianjin University, Tianjin 300072, P.R. China
Xue-Qin Zhou
School of Chemical Engineering, Tianjin University, Tianjin 300072, P.R. China

Corresponding Author(s) : Xue-Qin Zhou

zhouxueqin@tju.edu.cn

Asian Journal of Chemistry, Vol. 25 No. 5 (2013): Vol 25 Issue 5

Abstract

A mild and efficient procedure for Michael addition of a-bromochalcone with cyclohexanone has been developed. In the presence of sodium ethoxide, a-bromochalcone reacted with cyclohexanone to afford Michael products in moderate to high yield and good diastereoselectivities. Especially, while CH3CH2ONa or t-BuOK as catalyst, the unexpected products were obtained, which were the compound 4a((8aR,9S)-4a,8a-dihydroxy-10-phenyl-tetradecahydro-phenanthren-9-yl)(phenyl)methanone) and 4b(((8aR,9R)-4a,9-dihydroxy-10-phenyl-tetradecahydrophenanthren-9-yl)(phenyl)methanone).

Keywords

Cyclohexanone Synthesis α-Bromochalcone
Gao, L.-G., Liu, D.-Z., Li, W., & Zhou, X.-Q. (2012). A Mild and Efficient Procedure for Asymmetric Michael Additions of a-Bromochalcone with Cyclohexanone Catalyzed by Different Bases. Asian Journal of Chemistry, 25(5), 2561–2564. https://doi.org/10.14233/ajchem.2013.13457
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