22607-10-9Relevant articles and documents
Biocatalytic synthesis of non-vicinal aliphatic diols
Ebrecht, Ana C.,Aschenbrenner, Jasmin C.,Smit, Martha S.,Opperman, Diederik J.
supporting information, p. 439 - 445 (2021/01/29)
Biocatalysts are receiving increased attention in the field of selective oxyfunctionalization of C-H bonds, with cytochrome P450 monooxygenases (CYP450s), and the related peroxygenases, leading the field. Here we report on the substrate promiscuity of CYP505A30, previously characterized as a fatty acid hydroxylase. In addition to its regioselective oxyfunctionalization of saturated fatty acids (ω-1-ω-3 hydroxylation), primary fatty alcohols are also accepted with similar regioselectivities. Moreover, alkanes such as n-octane and n-decane are also readily accepted, allowing for the production of non-vicinal diols through sequential oxygenation. This journal is
Olefin-dependent discrimination between two nonheme HO-Fev=O tautomeric species in catalytic H2O2 epoxidations
Company, Anna,Feng, Yan,Gueell, Mireia,Ribas, Xavi,Luis, Josep M.,Que Jr., Lawrence,Costas, Miquel
supporting information; experimental part, p. 3359 - 3362 (2009/12/06)
A study was conducted to demonstrate olefin-dependent discrimination of two nonheme HO-Fev=O tautomeric species in catalytic H2O 2 epoxidations. Mechanistic studies were carried out under the condition of excess of olefin to minimize over-oxidation reactions and all reactions for the study were carried out under a N2 atmosphere to prevent auto-oxidation process due to presence of O2. It was observed that the diol/epoxide (D/E) ration for these reaction was dependent on the specific olefin and ranged from 3/2 (cyclooctene) to 6/1 (1-octene). The oxidation of cyclooctene using H218O2 revealed that only 28% of the oxygen atoms in the epoxide derived from H 2O2. Mechanistic results suggested that HO-Fe v=O oxidant need to be labeled before its reaction with substrates.
Diastereoselective reduction of acyclic hydroxyketones and diketones with an indium hydride reagent
Yamada, Masafumi,Horie, Tomoaki,Kawai, Masao,Yamamura, Hatsuo,Araki, Shuki
, p. 15685 - 15690 (2007/10/03)
Hydroxyketones and diketones have been reduced with lithium indium hydride to give meso-diols selectively. α-Hydroxyketones and α-diketones are reduced to meso-1,2-diols with high diastereoselectivities, whereas the selectivities of β-hydroxyketones and β-diketones are less satisfactory.