1312997-40-2Relevant academic research and scientific papers
Kinetic resolution of α-substituted alkanoic acids promoted by homobenzotetramisole
Yang, Xing,Birman, Vladimir B.
, p. 11296 - 11304 (2011/10/19)
A new method for catalytic nonenzymatic kinetic resolution of α-substituted alkanoic acids has been developed, which relies on their activation with DCC followed by enantioselective alcoholysis of the intermediate symm-anhydrides in the presence of the amidine-based catalyst homobenzotetramisole (HBTM). Moderate to excellent selectivity factors (s=5-96) have been obtained in the case of several classes of substrates, namely, α-aryl-, α-aryloxy/alkoxy-, α-halo-, α-azido-, and α-phthalimido-alkanoic acids. Under similar conditions, α-(arylthio/alkylthio)-alkanoic acids undergo dynamic kinetic resolution providing corresponding esters in up to 92 % ee and up to 93 % yield. Copyright
Nonenzymatic dynamic kinetic resolution of α-(arylthio)- and α-(alkylthio)alkanoic acids
Yang, Xing,Birman, Vladimir B.
, p. 5553 - 5555 (2011/07/09)
Dynamic solution: The title acids undergo dynamic kinetic resolution during an enantioselective esterification catalyzed by (S)-homobenzotetramisole ((S)-HBTM; see scheme). This method extends the scope of the carboxylic acid derivatives that are amenable to the nonenzymatic version of this transformation. Copyright
