Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide
| العنوان: | Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide |
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| المؤلفون: | Danielle R. Hirsch, Stacey E. Brenner-Moyer, Ryan P. Murelli, Katherine N. Fuhr |
| المصدر: | Organic Letters. 19:6356-6359 |
| بيانات النشر: | American Chemical Society (ACS), 2017. |
| سنة النشر: | 2017 |
| مصطلحات موضوعية: | Stereochemistry, Stereoisomerism, 4-Pyrone, 010402 general chemistry, 01 natural sciences, Biochemistry, Aldehyde, Catalysis, Article, Stereocenter, chemistry.chemical_compound, Physical and Theoretical Chemistry, chemistry.chemical_classification, Aldehydes, Cycloaddition Reaction, 010405 organic chemistry, Organic Chemistry, Temperature, Enantioselective synthesis, Heterocyclic Compounds, Bridged-Ring, Cycloaddition, 0104 chemical sciences, chemistry, Chromones, Ylide, Dimerization |
| الوصف: | The first catalytic enantioselective [5 + 2] dipolar cycloaddition of a 3-hydroxy-4-pyrone-derived oxidopyrylium ylide is described. These studies leveraged the recently recognized ability of oxidopyrylium dimers to serve as the source of ylide, which was found to be key to increasing yields and achieving enantiomeric excesses up to 99%. General reaction conditions were identified for an array of α,β-unsaturated aldehyde dipolarophiles. Reaction products possess four stereocenters, and subsequent reduction introduced a fifth contiguous stereocenter with total stereocontrol. |
| تدمد: | 1523-7052 1523-7060 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::083aec439b87b83604b47b7db08587d7 https://doi.org/10.1021/acs.orglett.7b03196 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi.dedup.....083aec439b87b83604b47b7db08587d7 |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 15237052 15237060 |
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