57557-60-5Relevant academic research and scientific papers
Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles
Lauder, Kate,Anselmi, Silvia,Finnigan, James D.,Qi, Yuyin,Charnock, Simon J.,Castagnolo, Daniele
supporting information, p. 10422 - 10426 (2020/07/24)
The enantioselective synthesis of α-thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α-thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good-to-excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.
Nonenzymatic dynamic kinetic resolution of α-(arylthio)- and α-(alkylthio)alkanoic acids
Yang, Xing,Birman, Vladimir B.
supporting information; experimental part, 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
Kinetic resolution of α-substituted alkanoic acids promoted by homobenzotetramisole
Yang, Xing,Birman, Vladimir B.
supporting information; experimental part, 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
