Design of a bisamidinium claisen rearrangement catalyst for monodentate substrates.
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.
Annamalai
Venkatachalam R
VR
Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
Linton
Elizabeth C
EC
Kozlowski
Marisa C
MC
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D026082:Singlet Oxygen / Q000737:chemistry
D007093:Imidazoles; D026082:Singlet Oxygen