Figure 4: Rationale for improved chirality transfer during an oxy-Cope rearrangement.

(a) The tandem-ylide formation/[2,3]-sigmatropic rearrangement between a diazoacetate (1) and allyl alcohol (S)-11 (2) to generate a 3-hydroxy-1,5-hexadiene (12) bearing vicinal stereocentres and (b) application toward stabilization of a chair-like transition state.