Beyond L-proline: Investigation of the properties of other natural amino acids in an organocatalytic warfarin synthesis
Year: 2024
Type: preprint
Abstract: Proline is indisputably the model organocatalytic amino acid. However, other naturally occurring amino acids remain a potent and perhaps overlooked source of organocatalytic potential. In this work, we investigate the capacity of various natural amino acids to promote enantioselectivity in a synthesis of warfarin. We have identified L- and D-arginine as enantioselective catalysts for this reaction and have developed a recrystallization method to isolate the enantiomers of warfarin with high enantiopurity. In addition, we use methylated derivatives of arginine provide insight into the reaction mechanism.
Source: ChemRxiv
Authors: Anna Wurz, Naomi Benson, Sierra Carr, Ketan Chamakura, Lizbeth Chirinos, Sydney Coll, Arhemy Franco-Gonzalez, Kayla Ivory, Hope Jankowski, Trinity Lamb, Shaya LeBauer, Grace McPherson, Thanh Nguyen, Jeimy Nolasco Guevara, Lily Parsad, Phuong Pham, Emma Piner, Kaci Richardson, Abdelhadi Bendjellal, Chelsea McRae, Robert Hughes
Institution: East Carolina University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4399648795