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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.