Efficient and convergent synthesis of (R)‐(−)‐10‐methyltridecan‐2‐one, the sex pheromone of the spotted cucumber beetle, by iron‐mediated chirality transfer

The synthesis of ( R )‐(−)‐10‐methyltridecan‐2‐one, the female sex pheromone of the southern corn root worm ( Diabrotica undecimpunctata howardi Barber) [( R )‐ 1 ] in high enantiome‐ric purity (ee ≥ 99%) and excellent overall yield (75%, five steps) is described. In the crucial step the stereogenic center is generated by nucleophilic addition of allyltrimethylsilane to an enantiopure planar chiral (π‐allyl)tetracarbonyl‐iron(1 + ) complex.