Partial reduction of annulated heterocycles as a general route to medium rings containing oxygen and nitrogen
| Autor: | and Ian D. Linney, Ali Raoof, Timothy J. Donohoe, Madeleine Helliwell |
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| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Models
Molecular Chiral auxiliary Birch reduction Molecular Structure Nitrogen Organic Chemistry Molecular Conformation chemistry.chemical_element Ring (chemistry) Biochemistry Oxygen chemistry.chemical_compound chemistry Heterocyclic Compounds Furan Organic chemistry Indicators and Reagents Physical and Theoretical Chemistry Cyclic amines |
| Popis: | The preparation of annulated furans and pyrroles is described as part of a general strategy for the synthesis of medium ring heterocycles. After Birch reduction, the corresponding dihydro compounds were oxidatively cleaved to produce medium ring ethers and amines in an efficient manner. This methodology was successfully applied to the formation of eight- and nine-membered cyclic ethers and nine-membered cyclic amines. Attaching a chiral auxiliary (bismethoxymethylpyrrolidine) to the furan allowed the formation of nine-membered ethers in 95% ee. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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