Issue 3, 2015

One pot domino reaction accessing γ-nitroesters: synthesis of GABA derivatives

Abstract

Michael addition of 1,3-dicarbonyl compounds to nitrostyrenes is efficiently promoted by hydrotalcite [Mg–Al] to afford the respective γ-nitrodicarbonyl adducts. Differently, the addition of Meldrum's acid leads to a direct access of γ-nitroesters through a one pot domino process. GABA derivatives (+/−)-phenibut and (+/−)-baclofen were readily synthesized from the respective nitro adducts.

Graphical abstract: One pot domino reaction accessing γ-nitroesters: synthesis of GABA derivatives

Supplementary files

Article information

Article type
Paper
Submitted
10 Sep 2014
Accepted
30 Oct 2014
First published
31 Oct 2014

New J. Chem., 2015,39, 1643-1653

Author version available

One pot domino reaction accessing γ-nitroesters: synthesis of GABA derivatives

F. F. Naciuk, D. Z. Vargas, C. R. M. D'Oca, C. C. Moro and D. Russowsky, New J. Chem., 2015, 39, 1643 DOI: 10.1039/C4NJ01552E

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