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Synlett 2009(2): 297-301
DOI: 10.1055/s-0028-1087672
DOI: 10.1055/s-0028-1087672
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Flexible Approach to Methyl (5S)-5-Alkyltetramate Derivatives
Further Information
Publication History
Received
26 August 2008
Publication Date:
15 January 2009 (online)


Abstract
Regioselective Grignard reagent additions to 3-methoxymaleimides and subsequent diastereoselective reductive dehydroxylation of the resulting N,O-acetals were studied. On the basis of these studies, a flexible and highly regio- and diastereoselective approach to methyl 5-alkyltetramate derivatives was disclosed. The method is the first direct and flexible asymmetric cationic synthon-based approach, and allows for the synthesis of various methyl (5S)-5-alkyltetramate derivatives that are otherwise inaccessible by the commonly used methods based on α-amino acids.
Key words
tetramates - Grignard reagents - alkylation - reduction - asymmetric synthesis
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- Supporting Information