A synthesis of β-oxonitriles is reported via the generation of R1R2CLiCN 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 α-mono or α,α-disubstituted cyanoketones. 15N- and 17O-NMR data are reported for selected compounds. This journal is

Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides / Mamuye, Ashenafi Damtew; Castoldi, Laura; Azzena, Ugo Gavino; Holzer, Wolfgang; Pace, Vittorio. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 13:7(2015), pp. 1969-1973. [10.1039/c4ob02398f]

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

MAMUYE, Ashenafi Damtew;AZZENA, Ugo Gavino;
2015

Abstract

A synthesis of β-oxonitriles is reported via the generation of R1R2CLiCN 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 α-mono or α,α-disubstituted cyanoketones. 15N- and 17O-NMR data are reported for selected compounds. This journal is
Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides / Mamuye, Ashenafi Damtew; Castoldi, Laura; Azzena, Ugo Gavino; Holzer, Wolfgang; Pace, Vittorio. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 13:7(2015), pp. 1969-1973. [10.1039/c4ob02398f]
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11388/178864
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