Liebigs Annalen

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

D Enders, B Jandeleit

Index: Enders, Dieter; Jandeleit, Bernd Liebigs Annalen, 1995 , # 7 p. 1173 - 1176

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Citation Number: 4

Abstract

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+) ...