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L-Proline Catalyzed Direct Synthesis of (E)-Nitroalkenes from Aldehydes in Aqueous Medium

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Abstract

Direct synthesis of conjugated nitroalkene via Henry condensation reaction in one-pot often leads to poor conversion and yield due to the reversible nature of β-nitroalcohol intermediate which undergoes reversible reaction in the basic medium. Here we report a synthesis of β-nitroalkene employing L-proline, a bifunctional catalyst, which directs the reaction of aldehyde with nitroalkane to take a different reaction path that is devoid of β-nitroalcohol intermediate. Ready availability, low-cost, and environmental compatibility of the catalyst, use of water as a solvent, simple reaction conditions, and good to excellent yields of nitroalkenes are some of the highlights of our protocol.

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Acknowledgements

The analytical services provided by Sophisticated Analytical Instrumentation Facility (SAIF), North Eastern Hill University, Shillong, India are acknowledged.

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  1. Department of Chemistry, North-Eastern Hill University, Shillong, 793022, India

    Rahul Mohanta,  Mezhubeinuo, Mandita Devi & Ghanashyam Bez

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  1. Rahul Mohanta
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  2. Mezhubeinuo
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  3. Mandita Devi
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  4. Ghanashyam Bez
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Correspondence to Ghanashyam Bez.

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Mohanta, R., Mezhubeinuo, Devi, M. et al. L-Proline Catalyzed Direct Synthesis of (E)-Nitroalkenes from Aldehydes in Aqueous Medium. Catal Lett 153, 3003–3008 (2023). https://doi.org/10.1007/s10562-022-04228-4

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