Les ?-c�tonitriles groupes protecteurs de la fonction amine. Pr�paration d'amino-alcools
| العنوان: | Les ?-c�tonitriles groupes protecteurs de la fonction amine. Pr�paration d'amino-alcools |
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| المؤلفون: | Mohamed Abarbri, Maurice Lamant, Alain Guignard |
| المصدر: | Helvetica Chimica Acta. 78:109-121 |
| بيانات النشر: | Wiley, 1995. |
| سنة النشر: | 1995 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Metal amides, Chemistry, Organic Chemistry, Biochemistry, Catalysis, Amino acid, Inorganic Chemistry, Hydrolysis, Nucleophile, Reagent, Drug Discovery, Organic chemistry, Physical and Theoretical Chemistry |
| الوصف: | β-Ketonitrile-Derived Protecting Groups of the Amino Function. Synthesis of Amino Alcohols The amino group of natural L-amino acid esters is protected by condensation with 2-oxocyclopentanenitrile (1) or 2-formyl-2-phenylacetonitrile (10). Only the ester group of the formed cyanoenamino esters 2 and 11 reacts with nucleophilic reagents such as organometallics (RMgX, RLi), borohydrides, or metal amides, whereas the cyanoenamino group is unchanged (Schemes 1 and 2). Cyanoenamino alcohols obtained by reduction of cyanoenamino esters 2 are hydrolyzed under acidic conditions to amino alcohols with retention of the configuration of the starting amino acid. This sequence of reactions allows to prepare derivatives of L-tyrosinol from (−)-L-tyrosine (see, e.g., Scheme 4). Cyanoenamino esters 11 are readily methylated at the N-atom to give N-methylated cyanoenamino esters (Scheme 3). This property is exploited on the way of a multistep procedure to obtain N-methylated amino alcohols homologous to natural (−)-(1R,2S)-ephedrine. |
| تدمد: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.19950780111 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::f7c2458fc36f8734b70506c1f6e6f3b0 https://doi.org/10.1002/hlca.19950780111 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi...........f7c2458fc36f8734b70506c1f6e6f3b0 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15222675 0018019X |
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| DOI: | 10.1002/hlca.19950780111 |