188806-18-0Relevant articles and documents
1,3-dipolar cycloaddition of C-(2-thiazolyl)nitrones to chiral acrylates. Synthesis of enantiopure α-amino-2-alkylthiazoles and 5-formylpyrrolidin-2-ones
Tejero, Tomas,Dondoni, Alessandro,Rojo, Isabel,Merchan, Francisco L.,Merino, Pedro
, p. 3301 - 3318 (1997)
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.