Menthol is a natural product that is a component of many different commerical products. The chemical structure of menthol includes a 6 membered carbocycle with 3 stereogenic centers. The (±)-menthylmagnesium chloride Grignard reagent can be prepared from (±)-menthol in 2-steps by reaction with Lucas' reagent and exposure to Mg<sup>0</sup>. The carbon-magnesium bond of menthylmagnesium chloride is stereochemically labile, and therefore the (±)-menthylmagnesium chloride Grignard reagent exists as two diastereomers. Here we present our study of the stereochemical outcome of the nucleophilic addtion of (±)-menthylmagnesium chloride with sp hybridized electrophiles.

Diastereoselectivity of the nucleophilic addition of (±)-menthylmagnesium chloride with sp hybridized electrophiles

251st National Meeting (2016)

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