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

Herein, we report the metal free and intramolecular hydrogen bonding (IMHB) directed (Z)-selective synthesis of amide substituted beta -aminoenones. Systematically, we confirm the role of dual IMHB (C&z.dbd; O...H-N) on the Z-direction using single-crystal X-ray analysis and 1D and 2D NMR studie...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2017-06, Vol.19 (11), p.2541-2545
Hauptverfasser: Subramaniam, Palaniraja, Ramasubbu, Chandrasekaran, Athiramu, Selvaraj
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Sprache:eng
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Zusammenfassung:Herein, we report the metal free and intramolecular hydrogen bonding (IMHB) directed (Z)-selective synthesis of amide substituted beta -aminoenones. Systematically, we confirm the role of dual IMHB (C&z.dbd; 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.
ISSN:1463-9262
1463-9270
DOI:10.1039/c7gc00909g