Bodmann, Kerstin and Bug, Thorsten and Steinbeisser, Sabine and Kreuder, Reinhard and Reiser, Oliver (2006) Electrochemical oxidation of 2-substituted piperidines as a key step towards the synthesis of hydroxylated γ-amino acids. Tetrahedron Letters 47 (13), pp. 2061-2064.
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2-Substituted piperidines containing different oxygenated side chain functionalities were investigated in the electrochemical, anodic methoxylation. Surprisingly, the configuration of the side chain has a strong influence on the outcome of the electrochemical oxidation. Subsequent elimination of methanol from the oxidation products leads to N-protected eneamides, which upon ozonolysis can be converted to N,N-bisprotected γ-amino aldehydes that are useful building blocks for further synthetic transformations.
|Date:||27 March 2006|
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Owner:||Helge Knüttel (ADMIN)|
|Deposited On:||06 Sep 2006|
|Last Modified:||05 Aug 2009 13:22|