An efficient gram-scale one-pot approach to 2-substituted malonates and related structures
is developed, starting from commercially available aldehydes and active methylene
compounds. The technique combines Knoevenagel condensation with the reduction of the
C=C bond in the resulting activated alkenes with the Zn–AcOH system. The relative
ease with which the C=C bond reduction occurs can be traced to the accepting abilities
of the substituents in the intermediate arylidene malonates.
Key words
electron transfer - malonate - reduction - reductive alkylation - zinc