A DFT study on the base-catalyzed allylic rearrangement reaction of enol phosphate.

ABSTRACT: Enol phosphates are important intermediates for synthesizing bioactive molecules with neighboring C[double bond, length as m-dash]C and C[double bond, length as m-dash]O motifs, and their synthesis via the Perkow reaction is a highly attractive approach. The allyl rearrangement process involved in the Perkow reaction plays a key role in regulating the Z/E configuration of enol phosphate products. Herein, the mechanism of the base-catalyzed allylic rearrangement reaction of enol phosphates was investigated using density functional theory (DFT) methods. The calculated results of the NEt₃-catalyzed rearrangement reaction show that it undergoes two proton transfer steps and that the rate-determining step is the first proton transfer step with a free energy barri

SUBMITTER: Wang K 

PROVIDER: S-EPMC12459237 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature