Tetrahedron p. 3301 - 3318 (1997)
Update date:2022-08-03
Topics:
Tejero, Tomas
Dondoni, Alessandro
Rojo, Isabel
Merchan, Francisco L.
Merino, Pedro
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.
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