Transition-metal-catalysed Grignard reaction of secondary allylic phosphates

Abstract
Regio- and stereo-chemistry of transition-metal-catalysed Grignard reactions of secondary allylic phosphates have been investigated. Best results for regioselective carbon–carbon bond formation at the γ-position of secondary allylic phosphates were attained when copper(I) iodide was used as the catalyst. The naturally occurring monoterpene alcohols, geraniol and the sex pheromone of the African Monarch, were synthesized as a demonstration of the synthetic utility of the newly developed coupling reaction.

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