Chemical Research in Chinese Universities ›› 2013, Vol. 29 ›› Issue (6): 1115-1118.doi: 10.1007/s40242-013-3136-1

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Simple and Efficient Procedure for Highly Diastereoselective Synthesis of trans-1, 1-Disubstituted-2, 6-diarylcyclohexane-4-ones

YU Ya-qin1, WANG Zhong-liang1,2   

  1. 1. Tianjin Key Laboratory of Water Resources and Environment, Tianjin Normal University, Tianjin 300387, P. R. China;
    2. State Key Laboratory of Environmental Geochemistry, Institute of Geochemistry, Chinese Academy of Sciences, Guiyang 550002, P. R. China
  • Received:2013-03-22 Revised:2013-05-28 Online:2013-12-01 Published:2013-06-24
  • Contact: WANG Zhong-liang E-mail:wangzhongliang_szy@163.com
  • Supported by:

    Supported by the Key Projects in the National Science & Technology Pillar Program of China(No.2012BAC07B02), the Program for New Century Excellent Talents in University, China(No.NCET-10-0954), the National Natural Science Foundation of China (No.41173096) and the Natural Science Foundation of Tianjin City, China(No.10SYSYJC27400).

Abstract:

A simple and efficient method has been developed for highly diastereoselective synthesis of trans-1,1-disubstituted-2,6-diarylcyclohexane-4-ones from dibenzalacetone and malononitril with trans-1,2-diami-nocyclohexane as catalyst. The substrate 1,5-diaryl-1,4-pentadien-3-ones and active methylene compounds proceeded to give the products with good to excellent yield within a short time.

Key words: Substituted cyclohexanone, Double Michael addition, Malononitrile