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

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 good asymmetric induction. The cycloadducts were converted into ho...

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Bibliographic Details
Published in:Tetrahedron 1997-03, Vol.53 (9), p.3301-3318
Main Authors: Tejero, Tomas, Dondoni, Alessandro, Rojo, Isabel, Merchán, Francisco L, Merino, Pedro
Format: Article
Language:English
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Summary: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 good 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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00040-9