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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 12
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Articles

The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with β-nitrostyrene catalyzed by L-Proline

Emmy M. OmarIntegrated Chemical BioPhysics Research (ICheBP), Faculty of Science, Universiti Putra Malaysia, Selangor, Malaysia; View further author information
,
Mohd Basyaruddin A. RahmanIntegrated Chemical BioPhysics Research (ICheBP), Faculty of Science, Universiti Putra Malaysia, Selangor, Malaysia; ;Department of Chemistry Faculty of Science, Universiti Putra Malaysia, Selangor, Malaysia; Correspondence[email protected]
View further author information
,
Bukuo NiDepartment of Chemistry, Texas A&M University-Commerce, Commerce, TX, USAView further author information
&
Allan D. HeadleyDepartment of Chemistry, Texas A&M University-Commerce, Commerce, TX, USAView further author information
Pages 1578-1591 | Received 23 Jan 2019, Published online: 03 May 2019
 
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Abstract

Michael addition reactions of n-pentanal with ß-nitrostyrene in achiral and chiral ionic liquids catalyzed by l-proline were studied. Results indicate anion plays an important role as weak coordination properties in the reactivity and stereoselectivity towards Michael product. 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Bmim][NTf2]) ionic liquid was found to be the best solvent media with a high yield (up to 90%) and a high diastereomeric ratio (syn/anti: 91/9), with moderate enantioselectivity (38% ee) among ten ionic liquids tested. The ionic liquid has been reusable over five numbers of cycles.

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Additional information

Funding

This work was supported by Universiti Putra Malaysia under the Research Grant Scheme (RUGS).

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