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Chemoselective N-Heterocyclic Carbene-Catalyzed Cross-Benzoin Reactions: Importance of the Fused Ring in Triazolium Salts

Steven M. Langdon, Myron M. D. Wilde, Karen Thai and Michel Gravel*

*Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada, Email:

S. M. Langdon, M. M. D. Wilde, K. Thai, M. Gravel, J. Am. Chem. Soc., 2014, 136, 7359-7542.

DOI: 10.1021/ja501772m

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Morpholinone- and piperidinone-derived triazolium salts catalyze highly chemoselective cross-benzoin reactions between aliphatic and aromatic aldehydes. The reaction scope includes a wide range of benzaldehyde derivatives with electron-donating and -withdrawing groups as well as branched and unbranched aliphatic aldehydes. Low catalytic loadings give excellent yields in these reactions.

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Highly Chemo- and Enantioselective Cross-Benzoin Reaction of Aliphatic Aldehydes and α-Ketoesters

K. Thai, S. M. Langdon, F. Bilodeau, M. Gravel, Org. Lett., 2013, 15, 2214-2217.

Key Words

Benzoin Condensation, Organocatalysis

ID: J48-Y2014