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Intramolecular Cycloaddition Reactions of ω-Unsaturated Chiral Nitrones

✍ Scribed by Jan Marcus; Johannes Brussee; Arne van der Gen

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 151 KB
Volume: 1998
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199811)1998:11<2513::aid-ejoc2513>3.0.co;2-u

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✦ Synopsis

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

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