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Chiral nitriles are valuable structural motifs found in numerous pharmaceuticals and natural products. This study presents an efficient method for synthesizing chiral nitriles via a cycloaddition reaction between -cyano-substituted ,-unsaturated aldehydes and 3-methyl-1-phenyl-1-pyrazole-5-amine. The transformation is catalyzed by -heterocyclic carbene (NHC) at low loadings, affording the corresponding chiral nitriles in good to excellent yields with excellent enantioselectivities.
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http://dx.doi.org/10.1021/acs.joc.5c01269 | DOI Listing |
RSC Adv
August 2025
Université d'Orléans, CNRS, UMR 7311, ICOA 45067 Orléans France
Herein, we report an optimized Pd/Cu bimetallic catalyst that facilitates the stereoselective allylic alkylation of secondary and tertiary nitriles under mild conditions. This method affords homoallylic nitriles with adjacent tri- and tetrasubstituted stereocenters. Using both racemic and enantioselective catalysts, the system exhibits high regio- and enantioselectivity (ee up to 91%).
View Article and Find Full Text PDFCarbohydr Res
November 2025
School of Chemistry, University of Hyderabad, Gachibowli, Hyderabad, 500046, India. Electronic address:
A diverse group of C-pyrrolyl furanoside derivatives were synthesized from chiral 5-(4-hydroxybutyl)pyrrole) derivatives, which intern obtained via the 3 + 2 cycloaddition of spirocyclic donor-acceptor cyclopropanes and nitriles. The suitably positioned benzyl group on the polyhydroxy alkyl chain of pyrrole derivative is efficiently underwent an intramolecular S1 substitution reaction in the presence of a catalytic amount of Lewis acid, BF OEt. The methodology offers the synthesis of various C-pyrrolyl furanoside derivatives in the form of anomeric mixtures.
View Article and Find Full Text PDFChem Sci
August 2025
Department of Chemistry, MIT 77 Massachusetts Ave. Cambridge MA 02139 USA
A mild and catalytic method for the direct conversion of carboxylic acids into their corresponding nitriles is reported. In contrast to common nitrile preparations that rely on hazardous cyanide and cyanogen precursors, the present protocol employs a P/P-catalyzed 'oxidation-reduction condensation' approach to effect iterative amidation/retro-Ritter reaction of carboxylic acids with 1-phenethylamine. Primary, secondary, tertiary, and aromatic carboxylic acids all undergo nitrilation in synthetically viable yields, including several pharmaceuticals and natural products.
View Article and Find Full Text PDFJ Org Chem
August 2025
Institute of Advanced Materials, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, China.
Chiral nitriles are valuable structural motifs found in numerous pharmaceuticals and natural products. This study presents an efficient method for synthesizing chiral nitriles via a cycloaddition reaction between -cyano-substituted ,-unsaturated aldehydes and 3-methyl-1-phenyl-1-pyrazole-5-amine. The transformation is catalyzed by -heterocyclic carbene (NHC) at low loadings, affording the corresponding chiral nitriles in good to excellent yields with excellent enantioselectivities.
View Article and Find Full Text PDFProtein Expr Purif
November 2025
Department of Biotechnology, School of Life Sciences, Babasaheb Bhimrao Ambedkar University, Lucknow, Uttar Pradesh, 226025, India. Electronic address:
Hydroxynitrile lyases (HNLs) play a vital role in the asymmetric synthesis of drug precursors and plant defence. In this study, an R-specific HNL (PycHNL) was isolated and purified from Pyrus communis (pear) seeds using ammonium sulphate precipitation, gel filtration, and ion exchange chromatography, achieving a 14.31 % yield and 6.
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