Domino [4 + 1]-annulation of α,β-unsaturated δ-amino esters with Rh(ii )–carbenoids – a new approach towards multi-functionalized N-aryl pyrrolidines
| Autor: | Anna Klinkova, David S. Giera, Lothar Hennig, Christoph Schneider, Jury J. Medvedev, Olesia S. Galkina, Valerij A. Nikolaev |
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| Rok vydání: | 2015 |
| Předmět: |
Annulation
Pyrrolidines Molecular Structure Amino esters Stereochemistry Aryl Organic Chemistry Esters Conjugated system Biochemistry Pyrrolidine chemistry.chemical_compound chemistry Cyclization Intramolecular force Organometallic Compounds Michael reaction Rhodium Amino Acids Physical and Theoretical Chemistry Methane Carbenoid |
| Zdroj: | Organic & Biomolecular Chemistry. 13:2640-2651 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | Catalytic decomposition of diazomalonates and other diazoesters using Rh(II)- and Cu(II)-complexes in the presence of α,β-unsaturated δ-(N-aryl)amino esters gives rise to the formation of multi-functionalized pyrrolidines with yields of up to 82%. The reaction apparently occurs as a domino process involving the initial N-ylide formation followed by intramolecular Michael addition to the conjugated system of amino esters to afford the pyrrolidine heterocycle. The whole process can also be classified as a [4 + 1]-annulation of the δ-amino α,β-unsaturated ester with the carbenoid intermediate. |
| Databáze: | OpenAIRE |
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