ChemInform Abstract Aldol reaction of the silylated ketone (I) with the α,β-unsaturated aldehyde (II) yields the adduct (III) which is subjected to the Claisen rearrangement reaction, forming 1,4-stereoselectively the ketone (V). 1,5-Stereoselection is achieved in the rearrangement of the acylated aldol adduct (X), obtained by monoprotection of the diol (VI) with tert-butyldimethylsilyl chloride (VII), followed by acylation of the alcohol (VIII) with propionyl chloride (IX). (X) gives either the 2,6-syn acid (XI) via the corresponding E-enolate or the 2,6-anti acid (XII) via an intermediate Z-enolate. Numerous further examples are given in the original paper.
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