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

^*此作品的通讯作者

化学与化工学院

Beijing Institute of Technology

科研成果: 期刊稿件 › 文章 › 同行评审

32 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	2113-2118
页数	6
期刊	Organic and Biomolecular Chemistry
卷	10
期	10
DOI	https://doi.org/10.1039/c2ob06434k
出版状态	已出版 - 14 3月 2012

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

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.",

author = "Zhou, {Zhi Ming} and Li, {Zhi Huai} and Hao, {Xiao Yan} and Jun Zhang and Xiao Dong and Liu, {Ying Qiang} and Sun, {Wen Wen} and Dan Cao and Wang, {Jin Liang}",

year = "2012",

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doi = "10.1039/c2ob06434k",

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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

PY - 2012/3/14

Y1 - 2012/3/14

N2 - 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.

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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JO - Organic and Biomolecular Chemistry

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ER -

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

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