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Abstract
A number of chiral allylic alcohols have been prepared and submitted to a Mitsunobu reaction with dithioacetic acid. Allyl dithioesters were deprotonated by LDA at −30°C and resulting enethiolates were quenched with iodomethane to afford quantitatively S-allyl ketenedithioacetals. These precursors undergo a thio-Claisen rearrangement under smooth conditions: room temperature or heating at 101°C. The diastereoselectivity of this sigmatropic shift was examined with respect to the nature of the two substituents at the stereogenic centre. With a methyl and a tert-butyl group a 75 : 25 ratio was observed and interpreted by steric hindrance. With various alkoxy groups we have observed a very modest selectivity in favour of the syn diastereoisomer.
Published Version
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