1148112-58-6Relevant articles and documents
Towards heterogeneous organocatalysis: Chiral iminium cations supported on porous materials for enantioselective alkene epoxidation
Bulman Page, Philip C.,Mace, Andrew,Arquier, Damien,Bethell, Donald,Buckley, Benjamin R.,Willock, David J.,Hutchings, Graham J.
, p. 2330 - 2339 (2013)
Enantiomerically pure iminium cations have been supported on a microporous support (zeolite Y) and on a mesoporous support (Al-MCM-41). These materials are effective asymmetric catalysts for the epoxidation of a range of aryl alkenes, giving high conversions quickly and with enantioselectivities similar to or in some cases even higher than are achievable using the corresponding iminium tetraphenylborates under homogeneous conditions. The catalysts can be simply recycled by filtration and washing. The methodology is illustrated in the synthesis of two natural products, (-)-(3′S)-lomatin and (+)-(3′S,4′R)-trans-khellactone, showing the general efficacy of our approach. The Royal Society of Chemistry 2013.
Asymmetric epoxidation using iminium salt organocatalysts featuring dynamically controlled atropoisomerism
Bulman Page, Philip C.,Bartlett, Christopher J.,Chan, Yohan,Day, David,Parker, Phillip,Buckley, Benjamin R.,Rassias, Geracimos A.,Slawin, Alexandra M. Z.,Allin, Steven M.,Lacour, Jerome,Pinto, Andre
, p. 6128 - 6138 (2012)
Introduction of a pseudoaxial substituent at a stereogenic center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived azepinium salt organocatalysts affords improved enantioselectivities and yields in the epoxidation of unfunctionalized alkenes. In the biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis is controlled by the interaction of this substituent with the chiral substituent at nitrogen.
