Methyl‐jasmonat: Ein kurzer Weg zum Naturstoff und seinem unnatürlichen Enantiomer <i>via</i> Palladium(0)‐induzierte, enantiodivergente Alkylierung von Cyclopent‐2‐en‐1,3‐diol‐Derivaten

Abstract

Methyl Jasmonate: A Short Synthesis of Naturally Occurring Methyl Jasmonate and its Unnatural Enantiomer via Enantiodivergent Alkylation of Cyclopent‐2‐ene‐1,3‐diol Derivatives by Palladium(0)‐Induced Reactions Palladium‐catalyzed alkylation of cyclopent‐2‐ene‐1,2‐diol derivatives like 2 is a useful method for enantiodivergent functionalization, resulting in both enantiomeric series of chiral building blocks. The chiral building blocks 3 and 13 can be transformed to methyl jasmonate ( 1 )and its unnatural enantiomer ent ‐ 1 , recent statement [1b] that 1 has no odour at all and that ‘methyl jasmonate's’ fragrance is actually due to its cis ‐isomer ent ‐11 has been confirmed also for the enantiomeric series.