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
Revue
Tetrahedron: Asymmetry
Volume
22
Pagination
1266–1273
ISSN
0957-4166
Soumis le 12 avril 2018