Ho_2010_Org.Biomol.Chem_8_3480

Reference

Title : Nitrile assisted, Bronsted acid catalyzed regio and stereoselective diarylphosphonylation of allyl silyl ethers - Ho_2010_Org.Biomol.Chem_8_3480
Author(s) : Ho CY , Chan CW , Wo SK , Zuo Z , Chan LY
Ref : Org Biomol Chem , 8 :3480 , 2010
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.

PubMedSearch : Ho_2010_Org.Biomol.Chem_8_3480
PubMedID: 20532352

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Citations formats

Ho CY, Chan CW, Wo SK, Zuo Z, Chan LY (2010)
Nitrile assisted, Bronsted acid catalyzed regio and stereoselective diarylphosphonylation of allyl silyl ethers
Org Biomol Chem 8 :3480

Ho CY, Chan CW, Wo SK, Zuo Z, Chan LY (2010)
Org Biomol Chem 8 :3480