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
Author(s)
Soldermann, Nicolas
Velker, Joerg
Neels, Antonia
Date issued
2007
In
Synthesis
Vol
15
From page
2379
To page
2387
Subjects
Diels-Alder reaction Ireland-Claisen rearrangement Stereoselective synthesis (stereoselective prepn. of Me tetrahydrophthalimide acetates via tandem Diels-Alder cycloaddn. and Ireland-Claisen rearrangement of phenylmaleimide and butadienyl(trialkylsilyl)ketene acetals) stereoselective prepn isoindoledionylacetate Diels Alder cycloaddn endo selective phenylmaleimide butadienylketene acetal rearrangement cycloaddn tandem isoindoledionylacetate prepn
Abstract
A new tandem reaction leads to bicyclic cyclohexene derivs., e. g. I, 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. [on SciFinder(R)]
Publication type
journal article