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, Jérôme and Pinto, André (2012) Asymmetric epoxidation using iminium salt organocatalysts featuring dynamically controlled atropoisomerism. The Journal of Organic Chemistry, 77 (14). pp. 6128-6138. ISSN 0022-3263

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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.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemistry of Materials and Catalysis Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Depositing User:	Users 2731 not found.
Date Deposited:	12 Apr 2013 20:59
Last Modified:	24 Sep 2024 08:53
URI:	https://ueaeprints.uea.ac.uk/id/eprint/42114
DOI:	10.1021/jo300915u

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