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7.1.5.3.9 Variation 9: Transformation of Allyl Phosphate Esters

DOI: 10.1055/sos-SD-007-00142

Ooi, T.; Maruoka, K.Science of Synthesis, (20047208.

Nonenzymic heterolysis of allyl phosphate esters with concurrent generation of a new SC bond can be realized by the reaction with dimethylaluminum alkanethiolates.[‌33‌] For instance, treatment of a geranyl or neryl phosphate ester in hexane with dimethyl­aluminum alkanethiolates results in the formation of sulfides in a regio- and stereospecific manner (Scheme 25).

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