A synthesis of beta-oxonitriles is reported via the generation of (RRCLiCN)-R-1-C-2 species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of alpha-mono or alpha,alpha-disubstituted cyanoketones. N-15- and O-17-NMR data are reported for selected compounds.

Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides / A.D. Mamuye, L. Castoldi, U. Azzena, W. Holzer, V. Pace. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 13:7(2015 Feb 21), pp. 1969-1973. [10.1039/c4ob02398f]

Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides

L. Castoldi
Secondo
;
2015

Abstract

A synthesis of beta-oxonitriles is reported via the generation of (RRCLiCN)-R-1-C-2 species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of alpha-mono or alpha,alpha-disubstituted cyanoketones. N-15- and O-17-NMR data are reported for selected compounds.
Amides; Cyanoketone; Methylation; Molecular Structure; Nitriles
Settore CHIM/06 - Chimica Organica
9-dic-2014
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/890700
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