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Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aldol Reaction with Product Separated via Host-guest Interaction

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Abstract

Chiral organocatalysts of 4-adamantane amide based on L-proline with double hydrogen potential were synthesized and used in asymmetric aldol reactions. The reactions were evaluated in toluene under‒20 °C. A series of aldol products was obtained from moderate to good yields(up to 98%) with excellent diastereoselectivities(up to >99:1) and enantioselectivities(up to >99%). The aldol products in the system were separated by α-cyclodextrin via host-guest interaction and determined by chiral HPLC. The catalyst could be reused up to five times. The 4-substitution position played an important role in diastereoselectivity and enantioselectivity.

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Authors and Affiliations

  1. College of Chemistry, Jilin University, Changchun, 130012, P. R. China

    Rui Wang, Zhonglin Wei, Jing Guo, Yusha Feng, Enjie Xu, Haifeng Duan, Yingjie Lin, Qingbiao Yang & Yaoxian Li

  2. China-Japan Union Hospital of Jilin University, Changchun, 130031, P. R. China

    Jianshi Du

Authors
  1. Rui Wang
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  2. Zhonglin Wei
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  3. Jing Guo
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  4. Yusha Feng
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  5. Enjie Xu
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  6. Haifeng Duan
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  7. Yingjie Lin
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  8. Qingbiao Yang
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  9. Jianshi Du
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  10. Yaoxian Li
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Corresponding authors

Correspondence to Qingbiao Yang or Jianshi Du.

Additional information

Supported by the National Natural Science Foundation of China(No.21174052) and the Natural Science Foundation of Jilin Province of China(Nos.20160101311JC, 20170101105JC).

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40242_2018_7364_MOESM1_ESM.pdf

Role of adamantane amide at C4 based on L-proline double-H potential organocatalyst in aldol reaction with product being separated via host-gust interation

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Wang, R., Wei, Z., Guo, J. et al. Role of Adamantane Amide Based on L-Proline Double-H Potential Organocatalyst in Aldol Reaction with Product Separated via Host-guest Interaction. Chem. Res. Chin. Univ. 34, 180–185 (2018). https://doi.org/10.1007/s40242-018-7364-2

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  • DOI: https://doi.org/10.1007/s40242-018-7364-2

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