ChemInform Abstract: Trimethylsilyl Cyanide ‐ A Reagent for Umpolung. Part 17. Diastereoselectivity in Nucleophilic Acylations of α‐Chiral Carbonyl Compounds with α,β‐Unsaturated Aldehydes After Umpolung.

Abstract The title reaction ‐ i.e. the reaction of carbonyl compounds such as (II) and (VI) with the anions of silyloxynitriles (I) obtained by umpolung of the corresponding aldehydes ‐ proceeds via the two key intermediates (III) and (IV).