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

✍ Scribed by Enders, Dieter ;Jandeleit, Bernd

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 514 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1995199507159

✦ Synopsis

Abstract

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.