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Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to beta-amino acids
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2008 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 7, 1153-1157 p.Article in journal (Refereed) Published
Abstract [en]

The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and a,p-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or gamma-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding beta-amino acids is also described.

Place, publisher, year, edition, pages
2008. no 7, 1153-1157 p.
Keyword [en]
organocatalysis, amination reactions, beta-amino acid synthesis, isoxazolidines, asymmetric catalysis
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-58561DOI: 10.1055/s-2007-990935ISI: 000255122800021OAI: oai:DiVA.org:su-58561DiVA: diva2:424806
Note
authorCount :5Available from: 2011-06-20 Created: 2011-06-03 Last updated: 2017-12-11Bibliographically approved

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