134080-50-5Relevant academic research and scientific papers
Lipase-catalyzed doubly enantioselective ring-opening resolution between alcohols and lactones: Synthesis of chiral hydroxyl esters with two stereogenic centers
Xia, Bo,Li, Yanyan,Cheng, Guilin,Lin, Xianfu,Wu, Qi
, p. 3448 - 3454 (2015/04/16)
A novel lipase B from Candida antarctica-catalyzed doubly enantioselective ring-opening resolution between racemic alcohols and lactones was developed. By using this strategy, three optically pure compounds including hydroxyl esters with two stereogenic centers and recovered alcohols and lactones were obtained simultaneously in high yields and ee. This process was used for the resolution of various racemic alcohols with different substituent groups and lactones with different ring sizes (four- and seven- membered lactones). The scale-up experiments were also successful. Moreover, molecular docking was performed to explain the molecular basis of this doubly enantioselective ring-opening resolution. As an attractive and efficient strategy, lipase-catalyzed doubly enantioselective ring-opening resolution will be widely used in the synthesis of optically pure hydroxyl esters with two stereogenic centers. Opening new doors: A novel lipase B from Candida antarctica-catalyzed doubly enantioselective ring-opening resolution between racemic alcohols and lactones is developed.
Yeast-Mediated Resolution of β-Keto Esters of Prochiral Alcohols
Hudlicky, Tomas,Tsunoda, Toshiya,Gadamasetti, Kumar G.,Murry, Jerry A.,Keck, Gary E.
, p. 3619 - 3623 (2007/10/02)
Several racemic alcohols were converted to their β-keto esters with diketene, and the resulting compounds were subjected to kinetic resolution by means of baker's yeast.The unreacted keto esters were separated from the reduced hydroxy esters by chromatography, and the products were analyzed for levels of enantiomeric excess.Chiral shift reagents, Mosher esters, and optical rotation of the enantiomers of the alcohols were the criteria used to determine the optical integrity of the resolved alcohols after hydrolysis of the esters.Absolute sterochemistry was determined for the resolution products of all the substrates.Some rationale is advanced to account for the observed levels of enantiomeric excess and for the apparent diastereospecifity of the enzymatic resolution.The utility of this process as means of resolution of prochiral alcohols as well as an application of such resolution to the preparation of both enantiomers of a pyrrolizidine alkaloid synthon are indicated.
