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Updated: Feb 22, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes
Luping Liu1, Hyejin Kim1, Youwei Xie1
1Max-Planck-Institut für Kohlenforschung , Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.
Abstract:
Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Brønsted acid catalysts of the hetero-Diels-Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereoselectivity is generally observed and a variety of scents and natural products can be easily accessed.
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