643-75-4Relevant articles and documents
Structural insights into the desymmetrization of bulky 1,2-dicarbonyls through enzymatic monoreduction
Rabuffetti, Marco,Cannazza, Pietro,Contente, Martina Letizia,Pinto, Andrea,Romano, Diego,Hoyos, Pilar,Alcantara, Andres R.,Eberini, Ivano,Laurenzi, Tommaso,Gourlay, Louise,Di Pisa, Flavio,Molinari, Francesco
supporting information, (2021/01/25)
Benzil reductases are dehydrogenases preferentially active on aromatic 1,2-diketones, but the reasons for this peculiar substrate recognition have not yet been clarified. The benzil reductase (KRED1-Pglu) from the non-conventional yeast Pichia glucozyma showed excellent activity and stereoselectivity in the monoreduction of space-demanding aromatic 1,2-dicarbonyls, making this enzyme attractive as biocatalyst in organic chemistry. Structural insights into the stereoselective monoreduction of 1,2-diketones catalyzed by KRED1-Pglu were investigated starting from its 1.77 ? resolution crystal structure, followed by QM and classical calculations; this study allowed for the identification and characterization of the KRED1-Pglu reactive site. Once identified the recognition elements involved in the stereoselective desymmetrization of bulky 1,2-dicarbonyls mediated by KRED1-Pglu, a mechanism was proposed together with an in silico prediction of substrates reactivity.
Iodine-catalyzed α,β-dehydrogenation of ketones and aldehydes generating conjugated enones and enals
Cao, Yuanjie,Chen, Tieqiao,Huang, Tianzeng,Liu, Long
, p. 8697 - 8701 (2020/06/08)
A transition metal-free α,β-dehydrogenation of ketones and aldehydes was developed. This reaction was conducted in a facile I2/KI/DMSO system to produce the corresponding unsaturated compounds in good to high yields. The gram-scale experiment also indicated the potential synthetic value of this new reaction in organic synthesis. In the reaction, DMSO acted as both solvent and mild oxidant.
LiBr/β-CD/IBX/H2O-DMSO: A new approach for one-pot biomimetic regioselective ring opening of chalcone epoxides to bromohydrins and conversion to 1,2,3-triketones
Verma, Nishant,Kumar, Sumit,Ahmed, Naseem
supporting information, p. 1110 - 1120 (2017/05/25)
Highly regioselective ring cleavage of chalcone epoxides to bromohydrins has been carried out in good yields with LiBr in the presence of β-CD using DMSO-H2O as solvent system. The ring-opened product, i.e., bromohydrin, was well adapted to IBX-mediated oxidation in such a fashion that the bromohydrins are transformed to their corresponding 1,2,3-triketones in moderate-to-good yields in one pot.
