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

Enders Dieter | Zendy; Jandeleit Bernd | Zendy

Premium

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

Author(s) -

Enders Dieter,

Jandeleit Bernd

Publication year - 1995

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.1995199507159

Subject(s) - chirality (physics) , pheromone , chemistry , sex pheromone , stereochemistry , botany , physics , biology , particle physics , chiral symmetry , nambu–jona lasinio model , quark

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research