Synthesis of Nβ-Substituted α,β-Diamino Acids via Stereoselective N-Michael Additions to a Chiral Bicyclic Dehydroalanine
| العنوان: | Synthesis of Nβ-Substituted α,β-Diamino Acids via Stereoselective N-Michael Additions to a Chiral Bicyclic Dehydroalanine |
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| المؤلفون: | Javier Marín, Nuria Mazo, Alberto Avenoza, María M. Zurbano, Jesús H. Busto, Marta I. Gutiérrez-Jiménez, Paula Oroz, Jesús M. Peregrina, Claudio D. Navo, Francisco Corzana, Juan Asenjo, Gonzalo Jiménez-Osés |
| المصدر: | The Journal of Organic Chemistry. 85:3134-3145 |
| بيانات النشر: | American Chemical Society (ACS), 2020. |
| سنة النشر: | 2020 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Alanine, Base (chemistry), Bicyclic molecule, 010405 organic chemistry, Stereochemistry, Organic Chemistry, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Amino acid, Catalysis, chemistry.chemical_compound, chemistry, Nucleophile, Dehydroalanine, Stereoselectivity |
| الوصف: | The highly diastereoselective 1,4-conjugate additions of several nitrogen nucleophiles to chiral bicyclic dehydroalanines have been assessed effectively at room temperature in good to excellent yields without needing any catalyst or additional base. This methodology is general, simple, oxygen and moisture tolerant, high-yielding, totally chemo- and stereoselective. This procedure offers an efficient and practical approach for the synthesis of Nβ-substituted α,β-diamino acids, such as 1-isohistidine, τ-histidinoalanine, β-benzylaminoalanine, β-(piperidin-1-yl)alanine, β-(azepan-1-yl)alanine, and fluorescent and ciprofloxacin-containing amino acid derivatives. |
| تدمد: | 1520-6904 0022-3263 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::e12a23e8c80684e04c03b02ed1af4f2f https://doi.org/10.1021/acs.joc.9b03020 |
| حقوق: | OPEN |
| رقم الأكسشن: | edsair.doi...........e12a23e8c80684e04c03b02ed1af4f2f |
| قاعدة البيانات: | OpenAIRE |
Find this issue from the American Chemical Society | تدمد: | 15206904 00223263 |
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