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

Mamuye, Ashenafi Damtew and Castoldi, Laura and Azzena, Ugo Gavino and Holzer, Wolfgang and Pace, Vittorio (2015) Chemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides. Organic & Biomolecular Chemistry, Vol. 13 (7), p. 1969-1973. ISSN 1477-0520. eISSN 1477-0539. Article.

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DOI: 10.1039/C4OB02398F

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. 15Nand 17O-NMR data are reported for selected compounds.

Item Type:Article
ID Code:10724
Status:Published
Refereed:Yes
Uncontrolled Keywords:β-oxonitriles synthesis, R1R2CLiCN species, Weinreb amides
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:Royal Society of Chemistry
ISSN:1477-0520
eISSN:1477-0539
Deposited On:30 Jan 2015 09:51

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