Redox Isomerization/(3+2) Allenoate Annulation by Auto‐Tandem Phosphine Catalysis
| Autor: | David W. Lupton, Jeremy T. Maddigan-Wyatt, Mitchell T. Blyth, Joel F. Hooper, Michelle L. Coote, Jhi Ametovski |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Annulation
Phosphines 010405 organic chemistry Organic Chemistry Enantioselective synthesis General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry Redox Catalysis 0104 chemical sciences chemistry.chemical_compound Isomerism Tosyl chemistry Crotonates Oxidation-Reduction Isomerization Phosphine |
| Zdroj: | Chemistry – A European Journal. 27:16232-16236 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202103224 |
| Popis: | A phosphine-catalyzed approach to pyrrolines has been developed that involves two mechanistically unlinked catalytic processes. The first involves the redox isomerization of amino crotonates to provide access to aliphatic tosyl imines, which then engage in a (3+2) annulation with various allenoates. The reaction shows generality, with 24 examples established, along with a low yielding and moderately enantioselective variant. Mechanistic studies indicate that the viability of the process is linked to the selection of catalysts with similar propensity to add to the two coupling partners. |
| Databáze: | OpenAIRE |
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