An Expedient and Practical Method for the Synthesis of a Diverse Series of Cyclopropane α-Amino Acids and Amines
| Autor: | André B. Charette, Ryan P. Wurz |
|---|---|
| Rok vydání: | 2004 |
| Předmět: |
Cyclopropanes
chemistry.chemical_classification Olefin fiber Molecular Structure Cyclopropanation Chemistry Organic Chemistry Iodobenzene Carboxylic Acids Nitro compound chemistry.chemical_element food and beverages General Medicine Zinc Chemical synthesis Catalysis Amino acid Cyclopropane chemistry.chemical_compound Nitro Organic chemistry Rhodium Amine gas treating Amines Amino Acids |
| Zdroj: | The Journal of Organic Chemistry. 69:1262-1269 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo035596y |
| Popis: | A practical synthesis for the preparation of a diverse series of cyclopropane alpha-amino acids is described. Nitrocyclopropane carboxylates can be readily prepared through treatment of alpha-nitroesters and iodobenzene diacetate or alpha-nitro-alpha-diazoesters with a Rh(II) catalyst and an olefin. Reduction of the nitro group using zinc/HCl in i-PrOH affords substituted cyclopropane alpha-amino esters in modest to high yields (54-99%). A "one-pot" procedure involving sequential cyclopropanation and reduction is described. The method can also be applied to the preparation of arylcyclopropyl amines (three examples). |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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