94416-79-2Relevant academic research and scientific papers
Addition of organomagnesium reagents to ring epoxy-ketones. IV. Cis and trans R-(+)-pulegone oxides
Sepulveda, Jose,Tortajada, Jose,Mestres, Ramon
, p. 237 - 240 (2007/10/02)
Ethyl and vinyl magnesium bromides added across the carbonyl group of the trans pulegone oxide 1 and afforded the substituted pulegol oxides 3 and 4.On prolonged reaction, the ethyl and vinyl adducts isomerized to the 3-substituted-3,4-epoxymethan-8-ols 9 and 10.The acetylenic Grignard reagent gave a ca 6:1 mixture of the ethynyl pulegol oxides 5 and 7.The reaction of the above reagents with cis pulegone oxide 2, afforded high yields of the substituted pulegol oxides 15, 16 and 17.Trans pulegone oxide 1 reacted more slowly and afforded lower yields of adducts than the cis isomer on reaction with any of the above Grignard reagents.This difference in reactivity was used for the kinetic resolutions of the diastereomers.Thus pure trans pulegone oxide 1 was recovered after briefly reacting diastereoisomeric mixtures of the oxides with the Grignard reagents at low temperature.
