Thermo-responsive chiral micelles as recyclable organocatalyst for asymmetric Rauhut-Currier reaction in water

Lei Xu, Li Zhou, Yan-Xiang Li, Run-Tan Gao, Zheng Chen, Na Liu and Zong-Quan Wu ()
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Lei Xu: Jilin University
Li Zhou: Hefei University of Technology
Yan-Xiang Li: Hefei University of Technology
Run-Tan Gao: Jilin University
Zheng Chen: Jilin University
Na Liu: Jilin University
Zong-Quan Wu: Jilin University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Developing eco-friendly chiral organocatalysts with the combined advantages of homogeneous catalysis and heterogeneous processes is greatly desired. In this work, a family of amphiphilic one-handed helical polyisocyanides bearing phosphine pendants is prepared, which self-assembles into well-defined chiral micelles in water and showed thermo-responsiveness with a cloud point of approximately 38.4 °C. The micelles with abundant phosphine moieties at the interior efficiently catalyze asymmetric cross Rauhut-Currier reaction in water. Various water-insoluble substrates are transferred to target products in high yield with excellent enantioselectivity. The yield and enantiomeric excess (ee) of the product generated in water are up to 90% and 96%, respectively. Meanwhile, the yields of the same R-C reaction catalyzed by the polymer itself in organic solvents is

Date: 2023
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DOI: 10.1038/s41467-023-43092-7

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