Syntheses of Enantiomerically Pure Cyclopent-2-ene-1-carboxylic Acid and (Cyclopent-2-enyl)acetic Acid by Enantioselective Palladium-Catalyzed Allylic Alkylations − Synthesis of Enantiomerically Pure (−)-Chaulmoogric Acid
| العنوان: | Syntheses of Enantiomerically Pure Cyclopent-2-ene-1-carboxylic Acid and (Cyclopent-2-enyl)acetic Acid by Enantioselective Palladium-Catalyzed Allylic Alkylations − Synthesis of Enantiomerically Pure (−)-Chaulmoogric Acid |
|---|---|
| المؤلفون: | Matthias Seemann, Steffen Kudis, Markus Schoeller, Guenter Helmchen |
| المصدر: | European Journal of Organic Chemistry. 2003:2122-2127 |
| بيانات النشر: | Wiley, 2003. |
| سنة النشر: | 2003 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Allylic rearrangement, Carboxylic acid, Organic Chemistry, Enantioselective synthesis, chemistry.chemical_element, General Medicine, Alkylation, Chaulmoogric acid, Medicinal chemistry, Dimethyl malonate, Catalysis, Acetic acid, chemistry.chemical_compound, chemistry, Organic chemistry, Physical and Theoretical Chemistry, Ene reaction, Palladium |
| الوصف: | Asymmetric Pd-catalyzed allylic alkylations of dimethyl malonate and diethyl 2-acetoxymalonate with 3-chlorocyclopentene, using phosphanyloxazolines 1 and ent-1 as chiral ligands, gave products (−)-2 and (+)-3b with 95 and 99.5% ee, respectively. Oxidative degradation of (+)-3b furnished (+)-(R)-cyclopent-2-ene-1-carboxylic acid [(+)-4] with > 99% ee. Alkylation product (−)-2 was transformed into enantiomerically pure (−)-(R)-(cyclopent-2-enyl)acetic acid [(−)-5] by three simple steps. Availability of (−)-5 enabled the first synthesis of enantiomerically pure (−)-chaulmoogric acid [(−)-9] in three steps. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003) |
| تدمد: | 1099-0690 1434-193X |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a1bab64df0caea6d8e071110e6710085 https://doi.org/10.1002/ejoc.200200700 |
| حقوق: | CLOSED |
| رقم الأكسشن: | edsair.doi.dedup.....a1bab64df0caea6d8e071110e6710085 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 10990690 1434193X |
|---|