Asymmetric synthesis of (R)- and (S)-4-methyloctanoic acids. A new route to chiral fatty acids with remote stereocenters
| Autor: | Lourdes Muñoz, Angel Guerrero, Gloria Rosell, Mª Pilar Bosch |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
chemistry.chemical_classification
Chiral auxiliary Stereochemistry Organic Chemistry Enantioselective synthesis Alkylation Catalysis Stereocenter Inorganic Chemistry chemistry.chemical_compound Stereospecificity Enantiopure drug chemistry Organic chemistry Physical and Theoretical Chemistry Enantiomer Alkyl |
| Zdroj: | Tetrahedron: Asymmetry. 20:420-424 |
| ISSN: | 0957-4166 |
| DOI: | 10.1016/j.tetasy.2009.02.041 |
| Popis: | The enantioselective synthesis of both enantiomers of 4-methyloctanoic acid, one major aggregation pheromone component of the rhinoceros beetles of the genus Oryctes and an important aroma compound, is described. The key step of the synthesis is based on a stereospecific alkylation with an alcohol-protected alkyl iodide using a pseudoephedrine derivative as a chiral auxiliary followed by subsequent removal of the auxiliary. Both enantiomers are obtained in excellent yields and enantioselectivities (93–94% ee). The strategy outlined allows preparation of a wide variety of enantiopure methyl-branched saturated and unsaturated fatty acids. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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