Reductive Dimerization of 2-Substituted Cyclopropane-1,1-dicarboxylates Using Samarium(II) Diiodide

概要

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In the presence of samarium diiodide, 2-aryl and 2-heteroaryl cyclopropane-1,1-dicarboxylic esters were readily dimerized to give 3,4-disubstituted 1,1,6,6-hexanetetracarboxylic esters as diastereomeric mixtures in moderate to good yields. The diastereomeric mixtures were separated by preparative HPLC and stereo-chemistries of the isolated meso and racemic compounds were determined on the basis of HPLC analysis on chiral stationary phases. Between the ^1H-NMR spectra of the separated diastereomers, the characteristic differences in the chemical shifts of the C2-H (C5-H) signals were observed and explained based on the MOPAC calculation.
公益社団法人日本薬学会の論文
1999-10-15