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Paper | Special issue | Vol 64, No. 1, 2004, pp.207-214
Published online, 30th July, 2004
DOI: 10.3987/COM-04-S(P)13
Stereoselective Synthesis of 4-Aminomethyl-3-hydroxyprolinols and Ring Expansion into Enantiopure Polyfunctionalized Piperidines

Abdallah Deyine, Jean-Marc Delcroix, and Nicole Langlois*

*Institut de Chimie des Substances Naturelles, C.N.R.S., 1 avenue de la Terrasse, Bat. 27, 91198 Gif sur Yvette, France


A stereoselective route was developed to synthesize enantiopure 3,4,5-trisubstituted piperidines in few steps. The functionalities were introduced starting from (S)-pyroglutaminol as chiral material. The method is based on the 1,3-dipolar cycloaddition of N-benzylnitrone to a derived bicyclic α,β-ethylenic lactam, followed by a ring enlargement of five to six membered nitrogen heterocycles through aziridinium ions.