Palladium-Catalyzed Decarboxylative Rearrangements of Allyl 2,2,2-Trifluoroethyl Malonates: Direct Access to Homoallylic Esters
| Autor: | Cara Cesario, Jerod Patzner, Lawrence P. Tardibono, Marvin J. Miller |
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| Rok vydání: | 2009 |
| Předmět: |
Molecular Structure
Chemistry Extramural Decarboxylation Organic Chemistry chemistry.chemical_element Biochemistry Catalysis Malonates Article Claisen rearrangement chemistry.chemical_compound Malonate Cyclization Molecule Organic chemistry Physical and Theoretical Chemistry Palladium Derivative (chemistry) |
| Zdroj: | Organic Letters. 11:4076-4079 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol901518g |
| Popis: | Homoallylic esters are obtained in a single transformation from allyl 2,2,2-trifluoroethyl malonates by using a Pd(0) catalyst. Facile decarboxylation of allyl 2,2,2-trifluoroethyl malonates is attributed to a decrease in pK(a) compared to allyl methyl malonates. Subsequent reduction of the homoallylic 2,2,2-trifluoroethyl ester provides a (hydroxyethyl)cyclopentenyl derivative that represents a key intermediate in the synthesis of carbocyclic nucleosides. A select allyl 2,2,2-trifluoroethyl malonate undergoes a decarboxylative Claisen rearrangement to provide a regioisomeric homoallylic ester. |
| Databáze: | OpenAIRE |
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