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Intramolecular Cycloaddition Reactions of ω-Unsaturated Chiral Nitrones (1998)

Marcus, Jan ; Brussee, Johannes ; van der Gen, Arne

Weinheim : Wiley-Blackwell

Liebigs Annalen 1998 (1998), S. 2513-2517

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ISSN: 1434-193X

Keywords: Asymmetric synthesis ; Chiral induction ; Cyanohydrin ; Cycloaddition ; Nitrone ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The intramolecular 1,3-dipolar cycloaddition of ω-un-saturated chiral nitrones is described. Starting materials for this reaction are O-protected chiral cyanohydrins, prepared by an R-oxynitrilase catalyzed asymmetric addition of hydrogen cyanide to ω-unsaturated aldehydes. Intramolecular cycloaddition, followed by reductive opening of the isoxazolidine ring, produced five- and seven-membered ring compounds with chiral hydroxy and amine functionalities of high enantiomeric purity in excellent yield.

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

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