A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C2-Symmetry

Yukio Yamamoto; Jun'ichi Hoshino; Yukiko Fujimoto; Junko Ohmoto; Seiji Sawada

doi:10.1055/s-1993-25852

Synthesis 1993; 1993(3): 298-302
DOI: 10.1055/s-1993-25852

paper

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A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C₂-Symmetry

Yukio Yamamoto^* , Jun'ichi Hoshino, Yukiko Fujimoto, Junko Ohmoto, Seiji Sawada

^*Department of Chemistry, College of Liberal Arts and Sciences, Kyoto University, Yoshida, Kyoto 606, Japan

Abstract

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By the use of (-)-1-phenylethylamine as a chiral auxiliary, three diastereomeric isomers of 2,5-bis(methoxycarbonyl)pyrrolidine derivatives are prepared from dimethyl rac-2,5-dibromoadipate and separated by crystallization and chromatographic fractionation involving stereoselective hydrolysis. The cis isomer is recovered and epimerized to the trans counterparts. Starting from each of the two trans isomers, optically active 2,5-disubstituted [2,5-bis(methoxymethyl) and 2,5-bis(methoxymethoxymethyl)] pyrrolidines of C ₂-symmetry are synthesized by a short route.

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