A Redox Auxiliary Strategy for Pyrrolidine Synthesis via Photocatalytic [3+2] Cycloaddition
| Autor: | Evan M. Sherbrook, Tehshik P. Yoon, Adrian G. Amador |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Ketone Tertiary amine 010405 organic chemistry Chemistry Organic Chemistry Photoredox catalysis 010402 general chemistry 01 natural sciences Combinatorial chemistry Redox Cycloaddition Pyrrolidine Article 0104 chemical sciences chemistry.chemical_compound Electrophile Photocatalysis |
| Zdroj: | Asian J Org Chem |
| ISSN: | 2193-5807 |
| Popis: | Cycloaddition reactions can be used to efficiently assemble pyrrolidine rings that are significant in a variety of chemical and biological applications. We have developed a method for the formal cycloaddition of cyclopropyl ketones with hydrazones that utlizes photoredox catalysis to enable the synthesis of a range of structurally diverse pyrrolidine rings. The key insight enabling the scope of photoredox [3+2] cycloadditions to be expanded to C=N electrophiles was the use of a redox auxiliary strategy that allowed for photoreductive activation of the cyclopropyl ketone without the need for an exogenous tertiary amine co-reductant. These conditions prevent the deleterious reductive ring-opening of the cyclopropyl substrates, enabling a range of less-reactive coupling partners to participate in this cycloaddition. |
| Databáze: | OpenAIRE |
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