Acta Chimica Sinica ›› 2012, Vol. 70 ›› Issue (10): 1201-1206.DOI: 10.6023/A1108182 Previous Articles     Next Articles

Full Papers


王利敏a, 程森祥a, 陈彤a, 常俊标a,b   

  1. a 河南省科学院高新技术研究中心 郑州 450002;
    b 郑州大学化学系 郑州 450001
  • 投稿日期:2011-08-18 修回日期:2012-01-04 发布日期:2012-05-16
  • 通讯作者: 常俊标;
  • 基金资助:

    国家杰出青年科学基金(No. 30825043)和国家自然科学基金(No. 20572017)资助项目.

Preparation of Axially Chiral Biphenyls by Configuration Transformation Based on Chiral Amino Alcohols

Wang Limina, Cheng Senxianga, Chen Tonga, Chang Junbiaoa,b   

  1. a Hi-tech. Research Center, Henan Academy of Sciences, Zhengzhou 450002;
    b Department of Chemistry, Zhengzhou University, Zhengzhou 450001
  • Received:2011-08-18 Revised:2012-01-04 Published:2012-05-16
  • Supported by:

    Project supported by the National Outstanding Young Scholar Science Foundation of National Natural Science Foundatiion of China (No. 30825043) and the National Natural Science Foundation of China (No. 20572017).

Axially chiral biphenyls (P, S)-3a and (M, R)-3b were obtained from (M/P)-4,4'-dimethoxy- 5,6,5',6'-bis(methylenedioxy)-2-carboxylester-2'-carboxamide biphenyls via configuration transformation of the biphenyls with (S)-alaninol or (R)-alaninol chiral-arm. Crystal structure of (P, S)-3a was determined. The crystal of (P, S)-3a belongs to monoclinic, space group P2(1), a=12.122(2) Å, b=8.9911(18) Å, c= 12.779(3) Å, β=112.38(3)°. There are two kinds of hydrogen-bonding in the (P, S)-3a crystal. The first is hydrogen-bonding between the hydroxyl group of the amino alcohol arm and the amide oxygen of a neighboring molecule. The second is hydrogen-bonding between the amide hydrogen atom and the amide oxygen of a neighboring molecule. Each molecule is linked to its two adjacent molecules by four intermolecular H-bonds. The configuration of (M, R)-3b was assigned based on the CD spectra. In addition, from (P, S)-3a, (P)-2,2'-dihydroxymethyl-4,4'-dimethoxy-5,6,5',6'-bis(methylenedioxy)-biphenyl (6a) was synthesized.

Key words: axially chiral biphenyl, crystallization induced, configuration transformation