1,3-DIPOLAR CYCLOADDITION OF C-(2-THIAZOLYL)NITRONES TO CHIRAL ACRYLATES - SYNTHESIS OF ENANTIOPURE ALPHA-AMINO-2-ALKYLTHIAZOLES AND 5-FORMYLPYRROLIDIN-2-ONES

Authors
TEJERO T DONDONI A ROJO I MERCHAN FL MERINO P
Citation
T. Tejero et al., 1,3-DIPOLAR CYCLOADDITION OF C-(2-THIAZOLYL)NITRONES TO CHIRAL ACRYLATES - SYNTHESIS OF ENANTIOPURE ALPHA-AMINO-2-ALKYLTHIAZOLES AND 5-FORMYLPYRROLIDIN-2-ONES, Tetrahedron, 53(9), 1997, pp. 3301-3318
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
9
Year of publication
1997
Pages
3301 - 3318
Database
ISI
SICI code
0040-4020(1997)53:9<3301:1COCTC>2.0.ZU;2-5
Abstract
The 1,3-dipolar cycloaddition of thiazolyl nitrones with chiral acryla tes has been studied. The use of the Oppolzer's camphor sultam as chir al inductor provided isoxazolidines with excellent regio- and diastere oselectivities and good asymmetric induction. The cycloadducts were co nverted into homochiral alpha-amino-2-alkylthiazoles and 5-(2-thiazoly l)-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. (C) 1997 Elsevier Science Ltd.