Synthesis and asymmetric hydrogenation of 3,5-dioxoheptanedioates. Preparation of enantiomerically pure substituted δ-valerolactones

The synthesis of 3,5-dioxoheptanedioic acid derivatives based on the reaction of ketene with malonyl chloride was developed. Resulting diketones were subjected to Ru–( S)-BINAP-catalyzed asymmetric hydrogenation. The products were transformed into enantiomerically pure 3,5-substituted-δ-valerolacton...

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Bibliographic Details
Published in:Tetrahedron letters 2000-06, Vol.41 (25), p.4959-4963
Main Authors: Kiegiel, Jarosław, Jóźwik, Julita, Woźniak, Krzysztof, Jurczak, Janusz
Format: Article
Language:English
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Summary:The synthesis of 3,5-dioxoheptanedioic acid derivatives based on the reaction of ketene with malonyl chloride was developed. Resulting diketones were subjected to Ru–( S)-BINAP-catalyzed asymmetric hydrogenation. The products were transformed into enantiomerically pure 3,5-substituted-δ-valerolactones.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)00747-4