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Exploiting intramolecular hydrogen bonding for the highly (Z)-selective & metal free synthesis of amide substituted β-aminoenones

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Abstract

Herein, we report the metal free and intramolecular hydrogen bonding (IMHB) directed (Z)-selective synthesis of amide substituted β-aminoenones. Systematically, we confirm the role of dual IMHB (C[double bond, length as m-dash]O⋯H–N) on the Z-direction using single-crystal X-ray analysis and 1D and 2D NMR studies. High stereoselectivity, atom efficiency, excellent yields and high purity are achieved by mere filtration. We avoid column purification and the formed by-product in the process is environmentally friendly.

Graphical abstract: Exploiting intramolecular hydrogen bonding for the highly (Z)-selective & metal free synthesis of amide substituted β-aminoenones

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Publication details

The article was received on 24 Mar 2017, accepted on 04 May 2017 and first published on 05 May 2017


Article type: Communication
DOI: 10.1039/C7GC00909G
Citation: Green Chem., 2017, Advance Article
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    Exploiting intramolecular hydrogen bonding for the highly (Z)-selective & metal free synthesis of amide substituted β-aminoenones

    P. Subramaniam, C. Ramasubbu and S. Athiramu, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC00909G

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