186707-59-5Relevant academic research and scientific papers
Development of the Julia asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters
Kroutil, Wolfgang,Lasterra-Sanchez, M. Elena,Maddrell, Samuel J.,Mayon, Patrick,Morgan, Phillip,Roberts, Stanley M.,Thornton, Steven R.,Todd, Christine J.,Tueter, Melek
, p. 2837 - 2844 (1996)
Polyleucine-based systems have been used to catalyse the asymmetric oxidation of a variety of alkyl enones 1-4, 9-14, an enynone 16 and a dienone 17 to afford the corresponding epoxides 5-8, 18-26 in good to excellent yield and optical purity. A range of enediones 30-32, 34 and one unsaturated keto ester 33 have also been epoxidised stereoselectively to afford optically active epoxides 35-39. The epoxidations were carried out with basic peroxide as the oxidant; the polyleucine catalyst was prepared from leucine N-carboxyanhydride using 1,3-diaminopropane, water (employing a humidity cabinet) or a polystyrene immobilised amine as the initiator. Preliminary mass spectral data on material derived from L-leucine and 1,3-diaminopropane (DAP-PLL) suggest that the catalyst consists of material that contains 22 ± 10 leucine residues.
Unexpected asymmetric epoxidation reactions catalysed by polyleucine-based systems
Kroutil, Wolfgang,Mayon, Patrick,Lasterra-Sanchez, M. Elena,Maddrell, Samuel J.,Roberts, Stanley M.,Thornton, Steven R.,Todd, Christine J.,Tueter, Melek
, p. 845 - 846 (2007/10/03)
Polyleucine-based systems have been shown to catalyse the asymmetric epoxidation of a variety of enones, an enynone, selected enediones and an unsaturated ketoester.
