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Stereoselective functionalisation of N-Boc pyroaminoadipic acid: Synthesis of 5-substituted aminoadipic and pipecolic acids

✍ Scribed by Jesús Ezquerra; Concepción Pedregal; Ana Escribano; M.Carmen Carreño; JoséL. García Ruano

Publisher
Elsevier Science
Year
1995
Tongue
French
Weight
244 KB
Volume
36
Category
Article
ISSN
0040-4039

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A stereoselective synthesis of N-Boc-protected cis-(2R,3S)-3-hydroxy pipecolic acid, starting from D-glucose is described. The key step in the overall synthesis is a highly regioselective reductive cleavage of benzylidene acetal 13 leading to hydroxymethyl piperidine derivative 14.