Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions

Zhi Ming Zhou; Zhi Huai Li; Xiao Yan Hao; Jun Zhang; Xiao Dong; Ying Qiang Liu; Wen Wen Sun; Dan Cao; Jin Liang Wang

doi:10.1039/c2ob06434k

Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions

Zhi Ming Zhou^*, Zhi Huai Li, Xiao Yan Hao, Jun Zhang, Xiao Dong, Ying Qiang Liu, Wen Wen Sun, Dan Cao, Jin Liang Wang

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

Functional imidazolium ionic liquids have been developed as a new class of versatile catalysts. C ₂-symmetric imidazolium-tagged bis(oxazoline) ligands were prepared, and the anions of the ligands were altered. The catalysts based on the new ligands and Cu(OAc) ₂·H ₂O were applied in asymmetric Henry reactions between various aldehydes 3 and CH ₃NO ₂4. The catalysts achieved a high level of enantioselectivity; product (R)-5n was attained at 94% ee in MeOH. Moreover, the catalyst could be recycled 6 times without an obvious loss of activity or enantioselectivity. In addition, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity.

Original language	English
Pages (from-to)	2113-2118
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	10
DOIs	https://doi.org/10.1039/c2ob06434k
Publication status	Published - 14 Mar 2012

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abstract = "Functional imidazolium ionic liquids have been developed as a new class of versatile catalysts. C 2-symmetric imidazolium-tagged bis(oxazoline) ligands were prepared, and the anions of the ligands were altered. The catalysts based on the new ligands and Cu(OAc) 2·H 2O were applied in asymmetric Henry reactions between various aldehydes 3 and CH 3NO 24. The catalysts achieved a high level of enantioselectivity; product (R)-5n was attained at 94% ee in MeOH. Moreover, the catalyst could be recycled 6 times without an obvious loss of activity or enantioselectivity. In addition, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity.",

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T1 - Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions

AU - Zhou, Zhi Ming

AU - Li, Zhi Huai

AU - Hao, Xiao Yan

AU - Zhang, Jun

AU - Dong, Xiao

AU - Liu, Ying Qiang

AU - Sun, Wen Wen

AU - Cao, Dan

AU - Wang, Jin Liang

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Y1 - 2012/3/14

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AB - Functional imidazolium ionic liquids have been developed as a new class of versatile catalysts. C 2-symmetric imidazolium-tagged bis(oxazoline) ligands were prepared, and the anions of the ligands were altered. The catalysts based on the new ligands and Cu(OAc) 2·H 2O were applied in asymmetric Henry reactions between various aldehydes 3 and CH 3NO 24. The catalysts achieved a high level of enantioselectivity; product (R)-5n was attained at 94% ee in MeOH. Moreover, the catalyst could be recycled 6 times without an obvious loss of activity or enantioselectivity. In addition, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity.

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Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions

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