Michael addition of 1,3-dicarbonyl compounds to nitrostyrenes is efficiently promoted by hydrotalcite [Mg-Al] to afford the respective g-nitrodicarbonyl adducts. Differently, the addition of Meldrum's acid leads to a direct access of g-nitroesters through a one pot domino process. GABA derivatives (+/À)-phenibut and (+/À)-baclofen were readily synthesized from the respective nitro adducts.
One Pot Domino Reaction Accessing -Nitroesters: Synthesis of GABA Derivatives. -Various -nitroesters are efficiently synthesized by Michael addition of 1,3-dicarbonyl compounds to nitrostyrenes using Mg-Al-hydrotalcite as catalyst. Compounds (VIII) are directly obtained from Meldrum's acid in an one-pot domino process. They are the starting material for the synthesis of GABA derivatives ()-phenibut (Xa) and ()-baclofen (Xf) which are obtained by subsequent reduction and hydrolysis. -(NACIUK, F. F.; VARGAS, D. Z.; D'OCA, C. R. M.; MORO, C. C.; RUSSOWSKY*, D.; New J. Chem. 39 (2015) 3, 1643-1653, http://dx.doi.org/10.1039/C4NJ01552E ; Inst. Quim., UFRGS, 9500 Porto Alegre, Rio Grande do Sul, Brazil; Eng.) -H. Toeppel 29-078
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