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Design of a bisamidinium claisen rearrangement catalyst for monodentate substrates
Venkatachalam R Annamalai1, Elizabeth C Linton, Marisa C Kozlowski
1Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Abstract:
A bisamidinium catalyst has been designed for the Claisen rearrangement. The primary design feature is a dual hydrogen bonding array that can coordinate a singular oxygen atom of the substrate. The ability to function as a dual hydrogen donor is key as the bisamidinium accelerates the Claisen rearrangement to a greater extent than Brønsted acids with lower pK(a) values.
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