• Chemistry, Medicine
  • Published in
    Beilstein journal of organic…
    2017
  • DOI:10.3762/bjoc.13.5

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

@inproceedings{Letzel2017DiastereoselectiveAH,
  title={Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates},
  author={Matthias C. Letzel and Hans J{\"u}rgen Sch{\"a}fer and Roland Froehlich},
  booktitle={Beilstein journal of organic chemistry},
  year={2017}
}
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… CONTINUE READING