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Andrei Yudin

Andrei Yudin

Academic Title: Professor

Blog: http://www.amphoteros.com

Phone: 416-946-5042

Office: DB 362


Research Homepage: http://www.chem.utoronto.ca/wp/yudinlab/


The Yudin group is well known for the development of new tools for chemical synthesis. In recent years, Yudin and his students have pioneered the chemistry of molecules that contain reactive, and usually incompatible, functional groups. This concept of “forced orthogonality” has enabled his lab to develop entirely new synthetic processes based on unprotected aziridine aldehydes (now commercially available through Sigma-Aldrich). These advances have been extensively published in the scientific literature and have been covered by the Chemical and Engineering News and worldwide ACS Webinars. In 2011, the Yudin lab has found a vast and unexplored class of molecules with coexisting α-C-B bonds and aldehyde groups. Following their discovery of α-boryl aldehydes (now commercially available from Sigma-Aldrich), the Yudin lab has developed 11 structurally distinct and new intermediates that were viewed as impossible to prepare, prior to their studies. Yudin and his students have also devised novel methods for making modified peptides, in particular peptide macrocycles, which is a long-standing challenge in synthesis. The molecules developed in the Yudin lab are valuable tool compounds in fragment screening using protein crystallography.

Selected Publications

Zajdlik, A.; Hickey, J.; Zhou, Z.; Schimmer, A.; Yudin, A. K. "Boryl isocyanides – reagents for facile preparation of bioactive boropeptides," Angew. Chem. Int. Ed. 2013, 52, 8411-8415.

He, Z; Yudin, A. K. "Amphoteric alpha-Boryl Aldehydes," J. Am. Chem. Soc. 2011, 133, 13770-13773.

Cheung, L.; He, Z.; Decker, S.; Yudin, A. K. "Skeletal Fusion of Small Heterocycles with Amphoteric Molecules," Angew. Chem. Int. Ed. 2011, 49, 11798-11802.

Dubovyk, I. D.; Pichugin, D.; Yudin, A. K. "Palladium-Catalyzed Ring Contraction and Ring Expansion Reactions of Cyclic Allyl Amines," Angew. Chem. Int. Ed. 2011, 50, 5924-5926.

White, C.; Yudin, A. K. "Contemporary Strategies for Peptide Macrocyclization," Nature Chem. 2011, 3, 509-524.

Jebrail, M. J.; Ng, A. H. C.; Rai, V.; Yudin, A. K.; Wheeler, A. R. "Synchronized Synthesis of Peptide-Based Macrocycles by Digital Microfluidics," Angew. Chem. Int. Ed. 2010, 49, 8625-8629.

He, Z.; Yudin, A. K. “A Versatile Synthetic Platform Based on Strained Propargyl Amines,” Angew. Chem. Int. Ed. 2010, 49, 1607-1610.

Hili, R.; Yudin, A. K. "Amphoteric Amino Aldehydes Reroute the aza-Michael Reaction," J. Am. Chem. Soc. 2009, 131, 16404-16406.

Hili, R. and Yudin, A. K. "Readily available unprotected amino aldehydes", J. Am. Chem. Soc. 2006 , 128 , 14772-14773

He, Z. and Yudin, A. K. "Palladium-Catalyzed Oxidative Activation of Cyclopropanes", Org. Lett. 2006 , 8 , 5829-5832

Alphonse, F. -A. and Yudin, A. K. "Rhodium-catalyzed stereoselective formation of Z - enamines from allyl aziridines", J. Am. Chem. Soc. 2006 , 128 , 11754-11755

Chen, G.; Sasaki, M.; Li, X.; Yudin, A. K. "Strained enamines as versatile intermediates for stereocontrolled construction of nitrogen heterocycles", J. Org. Chem. 2006 , 71 , 6067-6073

Hili, R. and Yudin, A. K. "Making carbon-nitrogen bonds in biological and chemical synthesis", Nature Chem. Biol. 2006 , 2 , 284-287

Watson, I. D. G.; Yu, L.; and Yudin, A. K. "Advances in nitrogen transfer reactions using aziridines", Acc. Chem. Res. 2006 , 39 , 194-206

Watson, I. D. G. and Yudin, A. K. "New insights into the mechanism of palladium-catalyzed allylic amination", J. Am. Chem. Soc. 2005 , 127 , 17516-17529