Facile Preparation of Novel Nonracemic Oxy‐Substituted Cyclopropanone S,S‐Acetals by γ‐Cyclisation of Glyceric Aldehyde Dithioacetal Derivatives and Studies of their Reactivity

Easily available glyceric aldehyde dithioacetals, (R)-1 and (R)-2, are converted via their tosylates, (R)-7a and b, and γ-elimination into nonracemic oxy-substituted cyclopropanone S,S-acetals, (R)-12 and (R)-13, in the presence of suitable electrophiles for trapping of alkoxide intermediates. Treatment of cyclopropanol (R)-14 with Burgess' reagent causes no 1,2-elimination, but a remarkable SN etherification with retention of configuration.

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