The High Stereoselectivity of the Tandem Sequence Diels-Alder Reaction/Ireland-Claisen Rearrangement Starting from Substituted O-(E)-Buta-1, 3-dienyl Ketene …

N Soldermann, J Velker, A Neels, H Stoeckli-Evans…

Index: Soldermann, Nicolas; Velker, Joerg; Neels, Antonia; Stoeckli-Evans, Helen; Neier, Reinhard Synthesis, 2007 , # 15 p. 2379 - 2387

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Abstract

Abstract 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.

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