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Updated: Jun 12, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Nitrile assisted, Brønsted acid catalyzed regio and stereoselective diarylphosphonylation of allyl silyl ethers
Chun-Yu Ho1, Chun-Wa Chan, Siu-Kwan Wo
1Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR. jasonhcy@cuhk.edu.hk
Abstract:
We have discovered a mild, catalytic protocol for the regio- and stereoselective synthesis of trisubstituted allyl diarylphosphonates from the corresponding disubstituted allyl silyl ethers, circumventing the challenges related to the preparation and availability of stereodefined trisubstituted olefins. A closely related arylation reaction was also discovered during the methodology development. By simply switching the reaction medium, high phosphonylation/arylation ratios and vice versa can be achieved. This may not be a direct result of changing solvent polarity. The allyl diarylphosphonates were evaluated as carboxylesterase inhibitors, and the screening results revealed that the inhibitory efficiency is highly related to the choice of alkenes and aryl substituents.
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