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Short Paper | Regular issue | Vol 87, No. 2, 2013, pp.381-388
Published online, 21st December, 2012
DOI: 10.3987/COM-12-12619
A Unique and Simple Preparative Method for α-Arylpipecolinic Acid Esters via Base-Induced Sommelet–Hauser Rearrangement

Eiji Tayama,* Ryota Sato, Motoshi Ito, Hajime Iwamoto, and Eietsu Hasegawa

*Department of Chemistry, Faculty of Sciences, Niigata University, Ikarasi 2-8050, Niigata 950-2181, Japan

Abstract

A unique and simple preparative method for N-cyano-α-arylpipecolinic acid esters via base-induced Sommelet–Hauser rearrangement, the von Braun reaction, and intramolecular α-alkylation is reported. The removal of the N-cyano substituent was achieved by hydrogenation and hydride reduction.