63559-26-2Relevant academic research and scientific papers
Biocatalytic Desymmetrization of Prochiral 3-Aryl and 3-Arylmethyl Glutaramides: Different Remote Substituent Effect on Catalytic Efficiency and Enantioselectivity
Ao, Yu-Fei,Zhang, Li-Bin,Wang, Qi-Qiang,Wang, De-Xian,Wang, Mei-Xiang
supporting information, p. 4594 - 4603 (2018/10/31)
Catalyzed by an amidase-containing Rhodococcus erythropolis AJ270 microbial whole cell catalyst in neutral phosphate buffer at 30 °C, desymmetric hydrolysis of a series of prochiral 3-aryl and 3-arylmethylglutaramides efficiently afforded 3-substituted glutaric acid monoamides in up to 95% yield and >99.5% ee. Even far away from the reaction site, the substituents on the aryl still have a significant effect on the catalytic activity and enantioselectivity and different remote substituent effect was observed for the two types of substrates. The synthetic application of biocatalytic desymmetrization was demonstrated by the facile transformation of the obtained enantiopure (R)-3-substituted 4-carbamoylbutanoic acid products to chiral dihydroquinolinone and δ-lactone compounds. (Figure presented.).
Asymmetric synthesis of (+)- and (-)-eptazocine via an enzymatic reaction
Shiotani, Shunsaku,Okada, Hirohiko,Yaroamoto, Takako,Nakamata, Kumiko,Adachi, Jun,Nakamoto, Hiromasa
, p. 113 - 126 (2007/10/02)
Starting from (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (R-(+)-4) prepared by enzymatic monoacetylation of 2-(p-methoxybenzyl)propane-1,3-diol (3) with lipase PS in the presence of vinyl acetate as an acetyl donor, lactones ( (+)- and (-)-6) were ob
