New N-Substituted Dipolarophiles in 1,3-Dipolar Cycloaddition of Nitrones

New N-Substituted Dipolarophiles in 1,3-Dipolar Cycloaddition of Nitrones

Abstract (N-Vinyl)-1,3-oxazolidin-2-ones, -1,3-oxazolidine-2-thi-ones and -N′-methylimidazolidin-2-one were conveniently used as new dipolarophiles in thermal 1,3-dipolar cycloaddition involving activated nitrones, and led to new 5-N-substituted isoxazolidines in high yields. A moderate to total TRA...

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Veröffentlicht in:Synlett 2006-12, Vol.2006 (19), p.3255-3258
Hauptverfasser: Nguyen, Thanh Binh, Gaulon, Catherine, Chapin, Teddy, Tardy, Sébastien, Tatibouët, Arnaud, Rollin, Patrick, Dhal, Robert, Martel, Arnaud, Dujardin, Gilles
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
letter
Organic chemistry
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Zusammenfassung:Abstract (N-Vinyl)-1,3-oxazolidin-2-ones, -1,3-oxazolidine-2-thi-ones and -N′-methylimidazolidin-2-one were conveniently used as new dipolarophiles in thermal 1,3-dipolar cycloaddition involving activated nitrones, and led to new 5-N-substituted isoxazolidines in high yields. A moderate to total TRANS-diastereoselectivity was observed, increasing with the degree of substitution at C-4.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-951545