230618-38-9Relevant articles and documents
The high stereoselectivity of the tandem sequence Diels-Alder reaction/Ireland-Claisen rearrangement starting from substituted O-(E)-buta-1,3-dienyl ketene acetals and cyclic dienophiles
Soldermann, Nicolas,Velker, Joerg,Neels, Antonia,Stoeckli-Evans, Helen,Neier, Reinhard
, p. 2379 - 2387 (2007)
A new tandem reaction leads to bicyclic cyclohexene derivatives with complete control of the relative configuration of the four chiral centers formed. The high diastereoselectivity is the consequence of an endo-selective Diels-Alder reaction followed by an Ireland-Claisen rearrangement that proceeds via a boat-like transition state. Georg Thieme Verlag Stuttgart.