1,3-dipolar cycloaddition of C-(2-thiazolyl)nitrones to chiral acrylates. Synthesis of enantiopure α-amino-2-alkylthiazoles and 5-formylpyrrolidin-2-ones

Article abstract of DOI:10.1016/S0040-4020(97)00040-9

The 1,3-dipolar cycloaddition of thiazolyl nitrones with chiral acrylates has been studied. The use of the Oppolzer's camphor sultam as chiral inductor provided isoxazolidines with excellent regio- and diastereoselectivities and goad asymmetric induction. The cycloadducts were converted into homochiral α-amino-2-alkylthiazoles and 5-(2-thiazolyl)-3-hydroxy-2-pyrrolidinones. The latter compounds were precursors of highly functionalized pyrrolidines by the aldehyde unmasking from the thiazole ring and subsequent reactions of the formyl group.