Inexpensive, multigram-scale preparation of an enantiopure cyclic nitrone via resolution at the hydroxylamine stage.
The redn. of the chiral, racemic nitrone 2-isopropyl-2,3-dimethyl-1-oxy-2,3-dihydroimidazol-4-one (MiPNO) provides a secondary hydroxylamine. Its O-acylation with O,O'-dibenzoyl-L-tartaric acid anhydride gives two diastereomers, that can be easily sepd. by selective dissoln. in orthogonal solvents. The recovery of the enantiopure nitrone is then carried out in a single step. The process allows the straightforward isolation of (R)- and (S)-MiPNO in 57{%} and 38{%} yield, resp., from rac-MiPNO. [on SciFinder(R)]
Références
- Titre
- Inexpensive, multigram-scale preparation of an enantiopure cyclic nitrone via resolution at the hydroxylamine stage.
- Type de publication
- Article de revue
- Année de publication
- 2011
- Auteurs
- Thiverny, Maryse, Demory Emilien, Baptiste Benoit, Philouze Christian, Chavant Pierre-Yves, and Blandin Véronique
- Revue
- Tetrahedron: Asymmetry
- Volume
- 22
- Pagination
- 1266–1273
- ISSN
- 0957-4166
Soumis le 12 avril 2018