Organocatalytic stereoselective additions of different nucleophiles to b-nitroacrylates have been investigated. A thiourea-based cinchona-derived bifunctional catalyst promotes the addition of 1,3-diketones to differently substituted nitroacrylates in modest to fair yields and up to 93% enantioselectivity. The 1,3 dicarbonyl functionality of the addition products was then used to synthesize enantiomerically enriched 3,4,5-trialkyl substituted pyrazoles via reaction with hydrazine. The stereoselective addition of Nmethylindole to nitroacrylate was also preliminarily studied; the Friedel–Crafts alkylation was successfully organocatalyzed in the presence of an acid additive in very good yields and up to 53% enantioselectivity.

Stereoselective Addition of 1,3-Diketones to b-Nitroacrylates Catalyzed by Chiral Metal-Free Bifunctional Catalysts

PALMIERI, Alessandro;
2014-01-01

Abstract

Organocatalytic stereoselective additions of different nucleophiles to b-nitroacrylates have been investigated. A thiourea-based cinchona-derived bifunctional catalyst promotes the addition of 1,3-diketones to differently substituted nitroacrylates in modest to fair yields and up to 93% enantioselectivity. The 1,3 dicarbonyl functionality of the addition products was then used to synthesize enantiomerically enriched 3,4,5-trialkyl substituted pyrazoles via reaction with hydrazine. The stereoselective addition of Nmethylindole to nitroacrylate was also preliminarily studied; the Friedel–Crafts alkylation was successfully organocatalyzed in the presence of an acid additive in very good yields and up to 53% enantioselectivity.
2014
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11581/313587
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