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Professor Andrei Yudin Professor Andrei Yudin

The Yudin laboratory is known for the development of amphoteric molecules and their application in synthesis. The corresponding reagents possess nucleophilic and electrophilic functional groups that do not prematurely react with each other. Over the years, Yudin and his students have developed a series of processes based on aziridine aldehydes, alpha-boryl aldehydes, and acyl boronates. These molecules have been applied in the synthesis of medicinally relevant heterocycles, macrocycles, and peptidomimetics. The mild reaction conditions, minimal reliance on protecting groups, and possibility to obtain scaffolds that are not accessible by other means are the main differentiating features of this technology.

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Ryan Hili, Andrei K Yudin
Journal of the American Chemical Society 2006-11-22
We report a new class of bench-stable compounds that contain seemingly incompatible functional groups: an aldehyde and an unprotected secondary amine. The thermodynamic driving force to undergo condensation between these two functionalities is offset by a high barrier imposed on this process by the aziridine ring strain. The res...Read More
Zhi He, Andrei K Yudin
Journal of the American Chemical Society 2011-09-07
A new class of stable molecules, α-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives that are difficult or impossib...Read More
Zhi He, Piera Trinchera, Shinya Adachi, Jeffrey D St Denis, Andrei K Yudin
Angewandte Chemie. International edition in English 2012-10-29
Excellent tolerance: Stable acylboronates equipped with N-methyliminodiacetyl (MIDA) boryl groups ([B]) were prepared by using a sequence of oxidative manipulations at the boron-bound carbon center (green in scheme). Chemoselective transformations of these acylated organoboron building blocks yielded a range of multifunctionaliz...Read More