Catalytic Asymmetric Intermolecular Stetter Reaction of Heterocyclic Aldehydes with Nitroalkenes: Backbone Fluorination Improves Selectivity
| العنوان: | Catalytic Asymmetric Intermolecular Stetter Reaction of Heterocyclic Aldehydes with Nitroalkenes: Backbone Fluorination Improves Selectivity |
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| المؤلفون: | Daniel A. DiRocco, Kevin M. Oberg, Tomislav Rovis, Derek M. Dalton |
| المصدر: | Journal of the American Chemical Society. 131:10872-10874 |
| بيانات النشر: | American Chemical Society (ACS), 2009. |
| سنة النشر: | 2009 |
| مصطلحات موضوعية: | Aldehydes, Halogenation, Molecular Structure, Stereoelectronic effect, Intermolecular force, Substituent, Stetter reaction, Stereoisomerism, General Chemistry, Alkenes, Nitro Compounds, Biochemistry, Combinatorial chemistry, Article, Catalysis, Organic Chemistry Phenomena, chemistry.chemical_compound, Colloid and Surface Chemistry, chemistry, Organic chemistry, Selectivity, Carbene |
| الوصف: | The catalytic asymmetric intermolecular Stetter reaction of heterocyclic aldehydes and nitroalkenes has been developed. We have identified a strong stereoelectronic effect on catalyst structure when a fluorine substituent is placed in the backbone. X-ray structure analysis provides evidence that hyperconjugative effects are responsible for a change in conformation in the azolium precatalyst. This new N-heterocyclic carbene precursor bearing fluorine substitution in the backbone results in significantly improved enantioselectivities across a range of substrates. |
| تدمد: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja904375q |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::200a905dc6427e5d97f91eb7aaa9bf9b https://doi.org/10.1021/ja904375q |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....200a905dc6427e5d97f91eb7aaa9bf9b |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15205126 00027863 |
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| DOI: | 10.1021/ja904375q |