10.1021/ol800298n
The research focuses on the construction of highly functionalized diazoacetoacetates through catalytic Mukaiyama?Michael reactions. The study involves the reaction between methyl 3-(trialkylsilanoxy)-2-diazo-3-butenoate and α,β-unsaturated enones, utilizing zinc(II) triflate as the optimal catalyst with a remarkably low loading of 0.1 mol %. The experiments conducted aimed to develop an efficient methodology for synthesizing complex diazo compounds under mild conditions, overcoming previous challenges associated with harsh reaction conditions and the instability of diazo compounds in the presence of Lewis acids. The researchers employed a series of catalyst screenings and optimizations, ultimately achieving good to excellent yields of vinyl ether and ketone derivatives. The analyses included monitoring the reaction progress, isolating the products, and characterizing them using spectroscopic data, which were detailed in the supporting information. This research significantly advances the field by providing a mild, efficient, and practical approach to synthesize diazoacetoacetates, which are valuable intermediates in organic synthesis.
