Convenient synthesis of an enantiomerically pure bicyclic proline and its N-oxyl derivatives

…, H Shiigi, H Mori, K Matsumoto, O Onomura

Index: Demizu, Yosuke; Shiigi, Hirofumi; Mori, Hiroyuki; Matsumoto, Kazuya; Onomura, Osamu Tetrahedron Asymmetry, 2008 , vol. 19, # 23 p. 2659 - 2665

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Citation Number: 15

Abstract

An enantiomerically pure bicyclic proline derivative was prepared by cis-selective allylation and diastereospecific intramolecular alkylation starting from d-pipecolinic acid. In addition, enantiomerically pure azabicyclo N-oxyls derived from the bicyclic proline worked well as catalysts for the enantioselective electrooxidation of racemic sec-alcohols to afford optically active sec-alcohols in moderate enantiomeric purity.

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