Asymmetric Epoxidation Using Iminium Salt Organocatalysts Featuring Dynamically Controlled Atropoisomerism

Philip C. Bulman Page, Christopher J. Bartlett, Yohan Chan, David Day, Phillip Parker, Benjamin R. Buckley, Geracimos A. Rassias, Alexandra M. Z. Slawin, Steven M. Allin, Jerome Lacour, Andre Pinto

Research output: Contribution to journalArticlepeer-review

38 Citations (Scopus)

Abstract

Introduction of a pseudoaxial substituent at a stereogenic center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived azepinium salt organo-catalysts 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.

Original languageEnglish
Pages (from-to)6128-6138
Number of pages11
JournalThe Journal of Organic Chemistry
Volume77
Issue number14
DOIs
Publication statusPublished - 20 Jul 2012

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