Asymmetric Epoxidation Using Iminium Salt Organocatalysts Featuring Dynamically Controlled Atropoisomerism
The Journal of Organic Chemistry2012Vol. 77(14), pp. 6128–6138
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Philip C. Bulman Page, Christopher Bartlett, Yohan Chan, David P. Day, Phillip Parker, Benjamin R. Buckley, Gerasimos Rassias, Alexandra M. Z. Slawin, Steven M. Allin, Jérôme Lacour, André Pinto
Abstract
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.
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