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Enantiodivergence by minimal modification of an acyclic chiral secondary aminocatalyst

Author

Listed:
  • Jun Dai

    (Yunnan University)

  • Zhuang Wang

    (Yunnan University)

  • Yuhua Deng

    (Yunnan University)

  • Lei Zhu

    (Chongqing University)

  • Fangzhi Peng

    (Yunnan University)

  • Yu Lan

    (Chongqing University)

  • Zhihui Shao

    (Yunnan University)

Abstract

The development of enantiodivergent catalysis for the preparation of both enantiomers of a chiral compound is of importance in pharmaceutical and bioorganic chemistry. With the design of a class of reactive and stereoselective organocatalysts, acyclic chiral secondary amines, a method for achieving the enantiodivergence is developed simply by changing the secondary N-i-Bu- to N-Me-group within the catalyst architecture while maintaining the same absolute configuration of the catalysts, which modulates the catalyst conformation. This catalyst-controlled enantiodivergent method not only enables challenging asymmetric transformations to occur in an enantiodivergent manner but also features a high level of stereocontrol and broad scope that is demonstrated in eight different reactions (90 examples), all delivering both enantiomers of a range of structurally diverse products including hitherto less accessible, yet important, compounds in good yields with high stereoselectivities.

Suggested Citation

  • Jun Dai & Zhuang Wang & Yuhua Deng & Lei Zhu & Fangzhi Peng & Yu Lan & Zhihui Shao, 2019. "Enantiodivergence by minimal modification of an acyclic chiral secondary aminocatalyst," Nature Communications, Nature, vol. 10(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-13183-5
    DOI: 10.1038/s41467-019-13183-5
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