Journal
NEW JOURNAL OF CHEMISTRY
Volume 42, Issue 24, Pages 20024-20031Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8nj04492a
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Funding
- Sichuan Agricultural University
- National Natural Science Foundation of China [51603064]
- Natural Science Foundation of Hubei province in China [2016CFB126]
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The synthesis of novel spiropyrrolidine oxindole derivatives was reported, using Ag-catalyzed [3+2] cycloaddition of azomethine ylides generated in situ from the condensation of substituted isatins and primary alpha-amino acid esters with chalcones. Products bearing four consecutive stereocenters, including spiroquaternary stereocenters fused in one ring structure, were smoothly acquired in moderate to high yields (50-95%) with good to excellent diastereoselectivities (11 : 1 -> 20 : 1 dr). Furthermore, product 4a underwent reduction, oxidation, hydrolysis and amidization to give the corresponding alcohol, dihydropyrrole, pyrrole, acid and amide, respectively, in good yields. The synthesized compounds (> 100 examples) were well characterized through different spectroscopic techniques, such as single crystal XRD, FTIR, NMR, and mass spectral analysis.
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