156. Lewis Acid-Catalyzed Tandem Diels−Alder Reaction/Retro-Claisen Rearrangement as an Equivalent of the Inverse Electron Demand Hetero Diels−Alder Reaction

Authors: Huw M. L. Davies and Xing Dai

J. Org. Chem.,

2005, 70 (17), 6680–6684

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A highly stereoselective formal inverse electron demand hetero Diels−Alder reaction (HDA) occurs on reaction of 2-aryl-α,β-unsaturated aldehydes with cyclopentadiene. The major pathway for this transformation is shown to be a Lewis acid-catalyzed tandem Diels−Alder reaction/retro-Claisen rearrangement.

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