Bioconjugation of carbohydrates has been a challenging task because of their chemical, functional, and structural diversities, and no single chemical modification tool can be universally applicable to all the target substrates in different environments. In this report, we have developed a bioconjugation strategy for labeling of carbohydrate derivatives through a phosphine-mediated three-component coupling reaction in an ionic liquid medium.
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Phosphine-mediated three-component bioconjugation of amino- and azidosaccharides in ionic liquids.
Chem Commun (Camb)
September 2022
Department of Chemistry, North Carolina State University, Raleigh, North Carolina, 27695, USA.
Bioconjugation of carbohydrates has been a challenging task because of their chemical, functional, and structural diversities, and no single chemical modification tool can be universally applicable to all the target substrates in different environments. In this report, we have developed a bioconjugation strategy for labeling of carbohydrate derivatives through a phosphine-mediated three-component coupling reaction in an ionic liquid medium.
View Article and Find Full Text PDFA phosphine-mediated domino sequence of salicylaldehyde with but-3-yn-2-one: rapid access to chromanone.
Org Biomol Chem
November 2020
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Chromanone is a privileged structure with a wide range of unique biological activities. A phosphine-promoted, three-component domino sequence of salicylaldehyde with but-3-yn-2-one was well designed for the construction of the chromanone skeleton under mild conditions. As a consequence, a series of novel chromanone analogues bearing an all-carbon quaternary center were facilely assembled from commercially available starting materials with moderate to good yields, which hold promising applications in pharmacological studies.
View Article and Find Full Text PDFStereoselective synthesis of polysubstituted alkenes through a phosphine-mediated three-component system of aldehydes, alpha-halo carbonyl compounds, and terminal alkenes.
Chemistry
June 2009
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, China.
Geometrical control: PPh(3) and methyl acrylate (or acrylamide) are able to mediate the one-pot Wittig reaction of aldehydes with alpha-halo carbonyl compounds for the synthesis of 1,2-disubstituted and trisubstituted alkenes in an excellent stereoselective fashion. Furthermore, the first one-pot, three-component reaction of aldehydes, alpha-halo acetates, and terminal alkenes has been developed in the presence of PPh(3) to produce trisubstituted alkenes with excellent E selectivity (see scheme).
View Article and Find Full Text PDFStable tetravalent phosphonium enolate zwitterions.
J Am Chem Soc
May 2007
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Three-component coupling reactions between trialkylphosphines, methyl propiolates, and aldehydes produced 1:1:1 dipolar adducts in moderate-to-excellent yields. The product phosphonium enolate zwitterions were isolated as crystalline solids. X-ray crystallographic analyses of these single crystals established unequivocally the dipolar structures of these tetravalent phosphonium enolate zwitterions.
View Article and Find Full Text PDFPhosphine-mediated reductive condensation of gamma-acyloxy butynoates: a diversity oriented strategy for the construction of substituted furans.
J Am Chem Soc
April 2004
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas, USA.
Exposure of gamma-acyloxy butynoates to stoichiometric quantities of triphenylphosphine results in reductive condensation to afford substituted furans, by way of allenic ester intermediates. As gamma-acyloxy butynoates are readily obtained through condensation of ethyl propiolate with aldehydes followed by acylation, this method represents a powerful and mechanistically novel protocol for the convergent three-component construction of substituted furans.
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