Synthesis of 4-Phosphinylpyrrolidin-3-ones via [3+2] Cycloaddition of Nitrones with Phosphinylallenes
A variety of 4-phosphinylpyrrolidin-3-ones was prepared via a [3+2] cycloaddition between aryl aldonitrones and phosphinylallenes. The products were isolated as unique 4,5-trans diastereomers, in yields between 47% and 80%, over 23 examples. In the case of chiral racemic allenes, a 2:1 to 4:1 moderate 2,5-diastereoselectivity was observed. Under the reaction conditions, the cycloadducts directly undergo a rearrangement to afford selectively the corresponding pyrrolidin-3-ones. DFT calculations provide some insights into the mechanism, involving the homolytic cleavage of the N−O bond of the cycloadduct.
Références
- Titre
- Synthesis of 4-Phosphinylpyrrolidin-3-ones via [3+2] Cycloaddition of Nitrones with Phosphinylallenes
- Type de publication
- Article de revue
- Année de publication
- 2023
- Auteurs
- Hammami, Rayhane, Maldivi Pascale, Philouze Christian, Carret Sébastien, Darses Benjamin, Touil Soufiane, and Poisson Jean-François
- Revue
- Advanced Synthesis & Catalysis
- Volume
- 365
- Ticket
- 9
- Pagination
- 1385-1390
- Mots-clés
- allenes Cycloaddition heterocycles Nitrones rearrangement
Soumis le 10 mai 2023