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Monofunctional primary amine: A new class of organocatalyst for asymmetric Aldol reaction

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Abstract

A new class of organocatalysts involving a primary amine as the only functional group is developed for catalytic asymmetric aldol reaction of cyclohexanone/cyclopentanone with various aryl aldehydes in the presence of benzoic acid as an additive at −10∘C. In an unexpected observation, the primary amine catalyzed reactions gave excellent yield and good to excellent stereoselectivity, while secondary amines were found to have little or no reactivity under similar reaction conditions.

A new class of aminocatalysts with a primary amine as the only catalytically active functional group was developed for catalytic asymmetric aldol reaction of cyclohexanone/cyclopentanone with various aryl aldehydes in the presence of benzoic acid as an additive at -10oC under neat conditions.

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Acknowledgements

Authors acknowledge the Council of Scientific and Industrial Research (CSIR), New Delhi, India for financial support (Scheme no. 1 (1992)/05/EMR-II). The analytical services provided by Sophisticated Analytical Instrumentation Facility, North Eastern Hill University, Shillong are gratefully acknowledged.

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  1. Department of Chemistry, North Eastern Hill University, Shillong, Meghalaya, 793 022, India

    KHIANGTE VANLALDINPUIA, PORAG BORA & GHANASHYAM BEZ

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  1. KHIANGTE VANLALDINPUIA
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  2. PORAG BORA
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Correspondence to GHANASHYAM BEZ.

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1H and 13C NMR spectra of new compounds and HPLC data are available free of charge at www.ias.ac.in/chemsci.

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VANLALDINPUIA, K., BORA, P. & BEZ, G. Monofunctional primary amine: A new class of organocatalyst for asymmetric Aldol reaction. J Chem Sci 129, 301–312 (2017). https://doi.org/10.1007/s12039-017-1237-y

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