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Synlett 2009(2): 297-301  
DOI: 10.1055/s-0028-1087672
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Flexible Approach to Methyl (5S)-5-Alkyltetramate Derivatives

Li-Jiao Jiang, Hong-Qiao Lan, Jian-Feng Zheng*, Jian-Liang Ye, Pei-Qiang Huang*
Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. of China
Fax: +86(592)2186400; e-Mail: pqhuang@xmu.edu.cn;
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Publication History

Received 26 August 2008
Publication Date:
15 January 2009 (online)

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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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