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Chiral Cu(II) Complexes as Recyclable Catalysts for Asymmetric Nitroaldol (Henry) Reaction in Ionic Liquids as Greener Reaction Media

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Abstract

Chiral Cu (II) complexes generated in situ from C2-symmetric chiral secondary bis-amines 1′–4′ based on 1,2-diaminocyclohexane structure having H, t-Bu and Cl substituents at 3, 3′, 4, 4′ and 5, 5′ with copper acetate. They were used as catalysts for an environmentally benign protocol for highly enantioselective nitroaldol reaction of various aldehydes with nitromethane in the presence of different ionic liquids as a greener reaction medium at 0 °C. Excellent yields (up to 90% with respect to aldehyde) of β-nitroalcohols with high enantioselectivity (ee, up to 94%) was achieved when [emim]BF4 was used as ionic liquid. The present ionic liquid mediated nitroaldol protocol is recyclable (up to five cycles) with no significant loss in its performance.

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Acknowledgment

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2009-0083525). N.H.K. thanks to KOFST for financial support through the Brain Pool program and also CSMCRI-CSIR India for sabbatical leave.

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Authors and Affiliations

  1. Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemical Fusion Technology, Department of Chemistry, Inha University, Incheon, 402-751, Korea

    Noor-ul Hasan Khan, Eko Adi Prasetyanto, Young-Ki Kim, Mohd Bismillah Ansari & Sang-Eon Park

  2. Discipline of Inorganic Materials and Catalysis, Central Salt and Marine Chemicals Research Institute (CSMCRI), Council of Scientific & Industrial Research (CSIR), G B Marg, Bhavnagar, 364-002, Gujarat, India

    Noor-ul Hasan Khan

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  1. Noor-ul Hasan Khan
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  2. Eko Adi Prasetyanto
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Correspondence to Sang-Eon Park.

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Khan, Nu.H., Prasetyanto, E.A., Kim, YK. et al. Chiral Cu(II) Complexes as Recyclable Catalysts for Asymmetric Nitroaldol (Henry) Reaction in Ionic Liquids as Greener Reaction Media. Catal Lett 140, 189–196 (2010). https://doi.org/10.1007/s10562-010-0443-8

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