1236212-76-2Relevant academic research and scientific papers
Direct carbon-carbon bond formation via soft enolization: A biomimetic asymmetric mannich reaction of phenylacetate thioesters
Kohler, Mark C.,Yost, Julianne M.,Garnsey, Michelle R.,Coltart, Don M.
supporting information; experimental part, p. 3376 - 3379 (2010/11/03)
(Equation Presented). An asymmetric Mannich reaction of phenylacetate thioesters and sulfonylimines using cinchona alkaloid-based amino (thio)urea catalysts is reported that employs proximity-assisted soft enolization. This approach to enolization is based on the cooperative action of a carbonyl-activating hydrogen bonding (thio)urea moiety and an amine base contained within a single catalytic entity to facilitate intracomplex deprotonation. Significantly, this allows thioesters over a range of acidity to react efficiently, thereby opening the door to the development of a general mode of enolization-based organocatalysis of monocarboxylic acid derivatives.
