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.

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

DONDONI, Alessandro;
1997

Abstract

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.
Tejero, T; Dondoni, Alessandro; Rojo, I; Merchan, Fl; Merino, P.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11392/1201460
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