Abstract
AbstractThe first asymmetric Carroll rearrangement opens up an efficient access to highly functionalised ketones 4 and 7 with vicinal quaternary and tertiary stereogenic centres of excellent diastereo‐ and enantiomeric purity (de =89–96%, ee =82 to >98%) by using the SAMP/RAMP hydrazone methodology. Starting from hydrazones (S)‐2, we describe a dianionic and a Lewis acid‐mediated variant of the [3.3]‐sigmatropic Carroll rearrangement. The relative and absolute configuration of the new stereogenic centres created by C–C bond formation were assigned by X‐ray crystallographic analysis of the hydrazones 3h and 3j.
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