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

Ashenafi Damtew Mamuye; Laura Castoldi; Ugo Azzena; Wolfgang Holzer; Vittorio Pace

doi:10.1039/c4ob02398f

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

Ashenafi Damtew Mamuye, Laura Castoldi, Ugo Azzena, Wolfgang Holzer, Vittorio Pace

Publications: Contribution to journal › Article › Peer Reviewed

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

Original language	English
Pages (from-to)	1969-1973
Number of pages	5
Journal	Organic & Biomolecular Chemistry
Volume	13
Issue number	7
DOIs	https://doi.org/10.1039/c4ob02398f
Publication status	Published - 21 Feb 2015

Austrian Fields of Science 2012

106002 Biochemistry

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10.1039/c4ob02398f

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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",

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T1 - Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides

AU - Mamuye, Ashenafi Damtew

AU - Castoldi, Laura

AU - Azzena, Ugo

AU - Holzer, Wolfgang

AU - Pace, Vittorio

PY - 2015/2/21

Y1 - 2015/2/21

N2 - 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

AB - 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

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DO - 10.1039/c4ob02398f

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AN - SCOPUS:84922611382

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JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

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ER -

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

Abstract

Austrian Fields of Science 2012

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