Chem. J. Chinese Universities ›› 1999, Vol. 20 ›› Issue (7): 1081.

• Articles • Previous Articles     Next Articles

Studies on Crystal Structure of Inclusion Chiral Crystal of (R)-Ethyl-2-pyridyl Sulfoxide with (4R,5R)-TADDOL

ZHU Jin1, ZHOU Zhong-Yuan1, FU Fang-Min1, DENG Jin-Geng1, MI Ai-Qiao1, JIANG Yao-Zhong1, QIU Tai-Yuan2   

  1. 1. Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041;
    2. Department of Chemistry, Chung-Hsing University, Taichung, 40227
  • Received:1998-07-23 Online:1999-07-24 Published:1999-07-24

Abstract: The synthesis and crystal structure of 1:1 inclusion chiral crystal formed from (R)-ethyl-2-pyridyl sulfoxide with (4R,5R)-α,α,α',α'-tetraaryl 1,3-dioxolane 4,5-dimethanol(TADDOL) were reported here. The crystal belongs to monoclinic, space group P21, a=0.9701(2) nm, b=0.9953(2) nm, c = 1.7392(2)nm; β=92.079°(14), V=1.6781(5)nm3, Mr= 621.76, Z=2, Dc= 1.230 g/cm3. The final refinement converges to R=0.0531 and Rw2= 0.0772 for 2335 observed independent reflections. Flack value is 0.1 (2). There is an intermolecular hydrogen bond in the inclusion crystal. Chiral TADDOL and ethyl-2-pyridyl sulfoxide(1) can be recognized each other in the inclusion crystal. Moreover, sulfoxide(1) in high enantiomeric excess was preparaed by resolution through inclusion complexation with the chiral TADDOL. The absolute configuration of (-)-ethyl-2-pyridyl sul-foxide was confirmed to be (R), which was assigned by the (R,R) absolute configuration of the TADDOL as an internal reference.

Key words: Chiral sulfoxide, TADDOL, Inclusion crystal

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