1148044-58-9Relevant academic research and scientific papers
Pyridylalanine (Pal)-peptide catalyzed enantioselective allenoate additions to N-acyl imines proceed via an atypical aza-Morita-Baylis-Hillman mechanism
Saunders, Lindsey B.,Cowen, Bryan J.,Miller, Scott J.
supporting information; experimental part, p. 4800 - 4803 (2011/01/03)
Mechanistic experiments, including kinetics and hydrogen/deuterium kinetic isotope effects, reveal an atypical rate-determining step in a pyridylalanine-peptide catalyzed enantioselective coupling of allenoates and N-acyl imines. Typically, acrylates participate in both the aldehyde-based Morita-Baylis-Hillman (MBH) reaction and the imine-based variant (the aza-MBH ) through similar mechanisms, with proton transfer/catalyst regeneration often rate-determining. In contrast, the title reaction exhibits kinetics wherein proton transfer is kinetically silent.
