(-)-Menthol as a source of new N,N-diamine ligands for asymmetric transfer hydrogenation |
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Authors: | Piotr Roszkowski Jan K Maurin Zbigniew Czarnocki |
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Institution: | 1. Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland;2. National Medicines Institute, Che?mska 30/34, 00-725 Warsaw, Poland;3. National Centre for Nuclear Research, So?tana 7, 05-400 Otwock-?wierk, Poland |
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Abstract: | The synthesis of new chiral N-monotosylated-1,2-diamines based on the (-)-menthol skeleton is presented. The elimination of HCl from neomenthyl chloride obtained from an Appel reaction led to p-menth-3-ene in excellent yield. Further functionalization of the double bond in p-menth-3-ene with chloramine-T gave the corresponding N-tosylaziridines, which upon reaction with sodium azide and subsequent reduction of the azide functional group, formed the 1,2-diamine system. The synthesized chiral ligands proved effective in the asymmetric transfer hydrogenation of aromatic ketones and an endocyclic imine. |
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Keywords: | Menthol Natural products Chiral diamines Asymmetric transfer hydrogenation Ruthenium complexes |
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