Highly enantioselective synthesis of 1,2-amino alcohol derivatives via proline-catalyzed Mannich reaction

Here we report a new catalytic asymmetric synthesis of oxazolidin-2-ones 4 and Cbz-protected 1,2-amino alcohols 5. Our sequence is based on the chemistry of previously unknown 5-acyloxy-oxazolidin-2-ones, which are obtained via proline-catalyzed direct asymmetric three-component Mannich reaction and...

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Bibliographic Details
Published inSynlett no. 12; pp. 1903 - 1905
Main Authors Pojarliev, P, Biller, WT, Martin, HJ, List, B
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 29.09.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
organocatalysis
multicomponent reactions
STYRENES
aminoalcohols
ASYMMETRIC AMINOHYDROXYLATION
SCOPE
ALPHA-AMINO-ACIDS
GLYCOL ALDEHYDE HYDRAZONES
oxazolidinones
SYNTHONS
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Summary:Here we report a new catalytic asymmetric synthesis of oxazolidin-2-ones 4 and Cbz-protected 1,2-amino alcohols 5. Our sequence is based on the chemistry of previously unknown 5-acyloxy-oxazolidin-2-ones, which are obtained via proline-catalyzed direct asymmetric three-component Mannich reaction and Baeyer-Villiger oxidation.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2003-41491