237081-53-7Relevant articles and documents
Enzymatic hydration of (18O)epoxides. Role of nucleophilic mechanisms.
Hanzlik,Edelman,Michaely,Scott
, p. 1952 - 1955 (1976)
-
Microbiological transformations. Part 48: Enantioselective biohydrolysis of 2-, 3- and 4-pyridyloxirane at high substrate concentration using the Agrobacterium radiobacter AD1 epoxide hydrolase and its Tyr215Phe mutant
Genzel,Archelas,Lutje Spelberg,Janssen,Furstoss
, p. 2775 - 2779 (2001)
The epoxide hydrolase (EH) from Agrobacterium radiobacter AD1 wild type (ArWT) and its Tyr215Phe mutant were compared for the biocatalyzed hydrolytic kinetic resolution (BHKR) of 2-, 3- and 4-pyridyloxirane. The regioselectivity of the oxirane ring opening as well as the substrate concentration limit and the inhibitory effect of the diol were determined. A gram scale preparation of enantiopure 2-pyridyloxirane (ee>98%) at a concentration as high as 127 mM (15.5 g/L) could be achieved with each of these two enzymes.
Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates
Von Keutz, Timo,Cantillo, David,Kappe, C. Oliver
supporting information, p. 7537 - 7541 (2020/10/12)
The generation of highly unstable chloromethylmagnesium chloride in a continuous flow reactor and its reaction with aldehydes and ketones is reported. With this strategy, chlorohydrins and epoxides were synthesized within a total residence time of only 2.6 s. The outcome of the reaction can be tuned by simply using either a basic or an acidic quench. Very good to excellent isolated yields, up to 97%, have been obtained for most cases (30 examples).
Manganese(II)/Picolinic Acid Catalyst System for Epoxidation of Olefins
Moretti, Ross A.,Du Bois,Stack, T. Daniel P.
supporting information, p. 2528 - 2531 (2016/07/06)
An in situ generated catalyst system based on Mn(CF3SO3)2, picolinic acid, and peracetic acid converts an extensive scope of olefins to their epoxides at 0 °C in 5 min, with remarkable oxidant efficiency and no evidence of radical behavior. Competition experiments indicate an electrophilic active oxidant, proposed to be a high-valent Mn = O species. Ligand exploration suggests a general ligand sphere motif contributes to effective oxidation. The method is underscored by its simplicity and use of inexpensive reagents to quickly access high value-added products.