TY - JOUR A1 - Letzel, Matthias C. A1 - Schäfer, Hans J. A1 - Fröhlich, Roland T1 - Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates JF - Beilstein Journal of Organic Chemistry PY - 2017/// VL - 13 SP - 33 EP - 42 SN - 1860-5397 DO - 10.3762/bjoc.13.5 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.13.5 KW - anodic decarboxylation KW - diastereoselectivity KW - Kolbe electrolysis KW - radical hetero-coupling KW - radical homo-coupling N2 - Diastereoselective radical coupling was achieved with chiral auxiliaries. The radicals were generated by anodic decarboxylation of five malonic acid derivatives. These were prepared from benzyl malonates and four menthol auxiliaries. Coelectrolyses with 3,3-dimethylbutanoic acid in methanol at platinum electrodes in an undivided cell afforded hetero-coupling products in 22–69% yield with a diastereoselectivity ranging from 5 to 65% de. Electrolyses without a coacid led to diastereomeric homo-coupling products in 21–50% yield with ratios of diastereomers being 1.17:2.00:0.81 to 7.03:2.00. The stereochemistry of the new stereogenic centers was confirmed by X-ray structure analysis and 13C NMR data. ER -